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Journal articles on the topic 'Bicyclo [5,2,1] décène'

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Published: 4 June 2021

Last updated: 17 February 2022

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1

Bonnaud, B., R. Leyssens, R. Viani, J. P. Aycard, and M. Monnier. "Dicarbonitrileméthylène-2 diméthyl-8,9 oxo-5 bicyclo[4.4.0]décène-8-cis." Acta Crystallographica Section C Crystal Structure Communications 43, no. 11 (November 15, 1987): 2248–49. http://dx.doi.org/10.1107/s0108270187088206.

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2

Nielsen, P., and F. Tarding. "The Metabolic Fate of 5-(bicyclo-3, 2, 1-oct-2-en-2-yl)-5-ethyl Barbituric Acid, (Reposal ®)." Acta Pharmacologica et Toxicologica 26, no. 6 (March 13, 2009): 521–30. http://dx.doi.org/10.1111/j.1600-0773.1968.tb00471.x.

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3

Pachuta-Stec, Anna, Urszula Kosikowska, Anna Chodkowska, Monika Pitucha, Anna Malm, and Ewa Jagiełło-Wójtowicz. "Biological Activity of Novel N-Substituted Amides of endo-3- (3-Methylthio-1,2,4-triazol-5-yl)bicyclo[2.2.1]hept-5-ene-2- carboxylic Acid and N-Substituted Amides of 1-(5-Methylthio- 1,2,4-triazol-3-yl)cyclohexane-2-carboxylic Acids." Zeitschrift für Naturforschung C 67, no. 3-4 (April 1, 2012): 123–28. http://dx.doi.org/10.1515/znc-2012-3-403.

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N-Substituted amides of endo-3-(3-methylthio-1,2,4-triazol-5-yl)bicyclo[2.2.1]hept-5-ene- 2-carboxylic acid and 1-(5-methylthio-1,2,4-triazol-3-yl)cyclohexane-2-carboxylic acid were prepared by the condensation reaction of endo-S-methyl-N1-(bicyclo[2.2.1]hept-5-ene-2,3- dicarbonyl)isothiosemicarbazide and S-methyl-N1-(cyclohexane-2,3-dicarbonyl)isothiosemicarbazide with primary amines. The synthesized compounds were screened for their microbiological and pharmacological activities

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4

Liu, Qi Mei, and Wan Xi Peng. "80°С-Based TD-GC/MS Analysis of Chemical Components from Branches of Cinnamomum camphora." Key Engineering Materials 480-481 (June 2011): 466–71. http://dx.doi.org/10.4028/www.scientific.net/kem.480-481.466.

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The analytical result by 80°С-based TD-GC/MS showed that 65 peaks were obtained from the helium volatiles from the fresh branches of Cinnamomum camphora and 60 chemical compounds were identified. The results showed that the main components were as: 1,3-Benzodioxole, 5-(2-propenyl)- (12.629%), Tricyclo[2.2.1.0(2,6)]heptane, 1,7-dimethyl-7-(4-methyl-3-pentenyl)-, (-)- (10.302%), 3-Cyclohexene-1-methanol, .alpha.,.alpha.4-trimethyl- (9.084%), Bicyclo[2.2.1] heptan-2-one, 1,7,7-trimethyl-, (1R)- (7.406%), Nerolidol (6.695%), Bicyclo[2.2.1]heptane, 2-methyl-3-methylene-2-(4-methyl-3-pentenyl)-, (1S-exo)- (6.017%), Bicyclo[2.2.1]heptan-2-one, 1,7,7-trimethyl-, (.+/-.)- (4.885%), Bicyclo[3.1.1]hept-2-ene, 2,6-dimethyl-6-(4-methyl-3-pentenyl)- (4.680%), Naphthalene, 1,2,3,5,6,8a-hexahydro-4,7-dimethyl-1-(1-methylethyl)-, (1S-cis)- (4.139%), 3-Cyclohexen-1-ol, 4-methyl-1-(1-methylethyl)-, (R)- (3.538%), Copaene (2.749%), Bicyclo[2.2.1] heptan-2-ol, 1,7,7-trimethyl-, (1S-endo)- (2.643%), Acetic acid, 1,7,7-trimethyl-bicyclo [2.2.1]hept-2-yl ester (2.536%), Cyclohexane, bromo- (2.530%), 1,6,10-Dodecatriene, 7,11- dimethyl-3-methylene-, (E)- (1.725%), Naphthalene, 1,2,3,4,4a,5,6,8a-octahydro-7-methyl-4- methylene-1-(1-methylethyl)-, (1.alpha.,4a.beta.,8a.alpha.)- (1.265%), Bicyclo[4.4.0]dec-1-ene, 2-isopropyl-5-methyl-9-methylene- (1.174%), (-)-Isosativene (1.149%), 11-Tetradecen-1-ol acetate (1.118%), .alpha.-Cadinol (1.061%), etc. The analytical result suggested that the helium volatiles from the fresh branches of C. camphora could be used as industrial materials of biomedicines, spicery and food industry.

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5

Petrov, Viacheslav A. "Stereoselective synthesis of 3-[(perfluoroprop-1-en-2-yl)bicyclo[2.2.1]-hept-5-en-2-yl]sulfanes." Mendeleev Communications 16, no. 3 (January 2006): 155–57. http://dx.doi.org/10.1070/mc2006v016n03abeh002327.

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6

Bourhis, Mireille, René Golse, Michel Goursolle, and Philippe Picard. "Synthesis of new norbornenones with the aminoester group methyl bicyclo [2-2-1] hept 5-ene 7-one 1-amino 2-carboxylates." Tetrahedron Letters 26, no. 29 (January 1985): 3445–48. http://dx.doi.org/10.1016/s0040-4039(00)98660-x.

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7

Ahlenstiel, Eckart, Wolfgang Kliegel, Steven J. Rettig, and James Trotter. "Structural studies of organoboron compounds. LVII. Synthesis and structure of bicyclic boron-nitrogen betaines. 1-Methyl-5-(3-nitrophenyl)-4,6,9-trioxa-1-azonia-5-boratabicyclo[3.3.1]nonane and 3,3,4-trimethyl-1-(3-nitrophenyl)-2,6,7-trioxa-3-azonia-1-boratabicyclo[2.2.2]octane." Canadian Journal of Chemistry 71, no. 2 (February 1, 1993): 263–71. http://dx.doi.org/10.1139/v93-038.

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The syntheses and structures of the bicyclic boron-nitrogen betaines 1-methyl-5-(3-nitrophenyl)-4,6,9-trioxa-1-azonia-5-boratabicyclo[3.3.1]nonane, 7a, and 3,3,4-trimethyl-1-(3-nitrophenyl)-2,6,7-trioxa-3-azonia-1-boratabicyclo[2.2.2]-octane, 14a, are reported. Crystals of 7a are orthorhombic, a = 20.256(2), b = 37.652(2), c = 6.642(1) Å, Z = 16, space group Fdd2, and those of 14a are orthorhombic, a = 21.402(2), b = 11.334(3), c = 11.248(2) Å, Z = 8, space group Pbca. The structures were solved by direct methods and were refined by full-matrix least-squares procedures to R = 0.038 and 0.045 (Rw = 0.036 and 0.053) for 975 and 1646 reflections with I ≥ 3σ(F2), respectively. The X-ray analyses establish the bicyclo[3.3.1]nonane and bicyclo[2.2.2]octane "cage" structures for 7a and 14a, respectively. Bond lengths involving the tetrahedral boron atom are (N)O—B = 1.519(5), (C)O—B = 1.444(6) and 1.443(6), C(aryl)—B = 1.602(5) Å for 7a; and (N)O—B = 1.530(3), (C)O—B = 1.446(3) and 1.455(3), C(aryl)—B = 1.608(3) Å for 14a. Weak [Formula: see text] interactions are the main feature of the crystal packing arrangements of both compounds.

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8

Werstiuk, Nick Henry, and Chandra Deo Roy. "Experimental and AM1 calculational studies of the deprotonation of bicyclo[2.2.2]octane-2,5-dione and bicyclo[2.2.2]octane-2,6-dione: a study of homoconjugation, inductive, and steric effects on the rates and diastereoselectivities of α enolization." Canadian Journal of Chemistry 73, no. 3 (March 1, 1995): 460–63. http://dx.doi.org/10.1139/v95-060.

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The kinetics of NaOD-catalyzed H/D exchange (enolization) at C3 α to the carbonyl group of bicyclo[2.2.2]octane-2,5-dione (1) and bicyclo[2.2.2]octane-2,6-dione (2) have been studied in 60:40 (v/v) dioxane–D2O at 25.0 °C. The second-order rate constants for exchange are (9.7 ± 1.5) × 10−1 and (3.4 ± 1.2) × 10−5 L mol−1 s−1 for 1 and 2, respectively. Thus, 1, exchanges 76 times faster than bicyclo[2.2.2]octan-2-one (3) (k = (1.27 ± 0.02) × 10−2 L mol−1 s−1), but the 2,6-dione 2 unexpectedly is much less reactive (2.7 × 10−3) than the monoketone. Unlike the large exo selectivity of 658 observed in the case of bicyclo[2.2.1]heptan-2-one, small and opposite selectivities, exo (1.2) for 1 and endo (2.1) for 2, are found for the isomeric [2.2.2] ketones. The results indicate that the incipient enolate of 1 is stabilized by a polar effect of the β carbonyl group at C5, not by homoconjugation. The source of the surprising low reactivity of 2 is unknown at this stage. The small diastereoselectivities, exo (1.2) for 1 and endo (2.1) for 2, correlate with relative energies of the diastereomeric pyramidal enolates calculated with AM1. Keywords: enolization, bicyclo[2.2.2]octane-2,5-dione, bicyclo[2.2.2]octane-2,6-dione, AM1, thermodynamic acidities.

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9

Werstiuk, N. H., S. Yeroushalmi, and Hong Guan-Lin. "Synthesis of bicyclic diones and thiones. Facile methylation of the enolates of bicyclo[2.2.1]heptane-2,5-dione and bicyclo[2.2.2]octane-2,5-dione. An AM1 computational study of bicyclic enolates." Canadian Journal of Chemistry 70, no. 3 (March 1, 1992): 974–80. http://dx.doi.org/10.1139/v92-130.

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A group of bicyclic ketones and thiones have been synthesized for homenolization studies. Bicyclo[2.2.1]heptane-2,5-dione (6) undergoes unusually rapid tetramethylation giving 3,3,6,6-tetramethylbicyclo[2.2.1]heptane-2,5-dione (1) in good yield. Treatment of 1 with P2S5 in xylene gave 3,3,6,6-tetramethylbicyclo[2.2.1]heptane-2,5-dithione (2) and 3,3,6,6-tetramethyl 15-oxo-bicyclo[2.2.1]heptane-2-thione (3), which was converted into 4 with Raney nickel. Bicyclo[2,2,2]octane-2,5-dione (7), prepared via a Diels–Alder reaction between 2-trimethylsilyloxy-1,3-cyclohexadiene and and α-acetoxyacrylonitrile followed by a one-step desilylation/hydrolysis, also undergoes facile tetramethylation giving 3,3,6,6-tetramethylbicyclo[2.2.2]octane-2,5-dione (5) in good yield. AM1 calculations were carried out on the α-enolates of bicyclo[2.2.1]heptan-2-one, 6, 5-methylidenebicyclo[2.2.1]heptan-2-one, and 4-acetylbicyclo[2.2.1]-heptan-2-one in an attempt to gain information on the source of the enhanced acidity of the C-3 hydrogens of 6 and 7. Keywords: bicyclic ketones, thiones, synthesis.

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10

Liu, Qi Mei, Dang Quan Zhang, Kuan Peng, and Wan Xi Peng. "Deep Analysis on Bioindustry Prospects of 40°С Volatiles of Cinnamomum camphora Branches." Key Engineering Materials 480-481 (June 2011): 266–71. http://dx.doi.org/10.4028/www.scientific.net/kem.480-481.266.

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Cinnamomum camphora has been used to heal some specific diseases in the Chinese Folk for a long time. In order to explore the wide utilization in biomedicine and spicery, the chemical components of helium volatiles from the fresh branches of C. camphora were studied by TD-GC/MS. The analytical result by TD-GC/MS showed that 50 peaks were obtained from the helium volatiles from the fresh branches of C. camphora and 46 chemical compounds representing 99.993% of the total areas were identified. The results showed that the main components were as: Bicyclo[2.2.1]heptan-2-one, 1,7,7-trimethyl-, (1R)- (9.620%), 3-Cyclohexene-1- methanol, .alpha.,.alpha.4-trimethyl- (9.425%), 1,3-Benzodioxole, 5-(2-propenyl)- (8.223%), Bicyclo[2.2.1]heptane, 2-methyl-3-methylene-2-(4-methyl-3-pentenyl)-, (1S-exo)- (7.541%), Tricyclo[2.2.1.0(2,6)]heptane, 1,7-dimethyl-7-(4-methyl-3-pentenyl)-, (-)- (6.884%), Bicyclo[3.1.1] hept-2-ene, 2,6-dimethyl-6-(4-methyl-3-pentenyl)- (6.050%), Bicyclo[2.2.1]heptan-2-one, 1,7,7- trimethyl-, (1S)- (4.678%), 1,3-Benzodioxole, 5-(2-propenyl)- (4.500%), Naphthalene, 1,2,3,5,6,8a- hexahydro-4,7-dimethyl-1-(1-methylethyl)-, (1S-cis)- (4.491%), 3-Cyclohexen-1-ol, 4-methyl-1- (1-methylethyl)-, (R)- (4.254%), Copaene (4.120%), Tricyclo[2.2.1.0(2,6)]heptane, 1,7-dimethyl-7- (4-methyl-3-pentenyl)-, (-)- (4.097%), Acetic acid, 1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester (3.574%), Borneol 3.334%), 3-(4-N,N-Dimethylaminophenyl)propenoic acid, 2- (diethoxyphosphinyl)-, ethyl ester (2.809%), Eucalyptol (2.096%), 1,6,10-Dodecatriene, 7,11- dimethyl-3-methylene-, (Z)- (1.885%), (-)-Isosativene (1.664%), 1,6,10-Dodecatrien-3-ol, 3,7,11-trimethyl- (1.407%), Cyclohexene, 1-methyl-4-(5-methyl-1-methylene-4-hexenyl)-, (S)- (1.218%), 1,4-Methanoazulene, decahydro-4,8,8-trimethyl-9-methylene-, [1S-(1.alpha.,3a.beta., 4.alpha.,8a.beta.)]- (1.174%), .alpha.-Caryophyllene (1.156%), etc. The analytical result suggested that the helium volatiles from the fresh branches of C. camphora can be applicable to biomedicine and spicery industrial materials.

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11

Saito, Nozomi, Yuki Tanaka, and Yoshihiro Sato. "Ruthenium-Catalyzed [2 + 2] Cycloaddition of Allenynes Leading to a Bicyclo[4.2.0]octa-1(8),5-diene Skeleton." Organic Letters 11, no. 18 (September 17, 2009): 4124–26. http://dx.doi.org/10.1021/ol901616b.

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12

Hřebabecký, Hubert, Milena Masojídková, Martin Dračínský, and Antonín Holý. "Synthesis of Novel Conformationally Locked Carbocyclic Nucleosides Derived from 3-(Hydroxymethyl)bicyclo[2.2.1]heptane-2,5-diol." Collection of Czechoslovak Chemical Communications 71, no. 6 (2006): 871–88. http://dx.doi.org/10.1135/cccc20060871.

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(1R*,2R*,3R*,4R*,5R*,6S*)-3-Amino-5-(benzyloxy)-6-(hydroxymethyl)bicyclo[2.2.1]heptan-2-ol (18) was prepared in seven easy steps from benzyl (1R*,2S*,3S*,4S*)-3-(benzyloxy)bicyclo[2.2.1]hept-5-ene-2-carboxylate (10). Reaction of amine18with ethylN-((2E)-3-ethoxymethacryloyl)carbamate afforded 1-[(1R*,2R*,3R*,4R*,5S*,6R*)-6-(benzyloxy)-3-hydroxy-5- (hydroxymethyl)bicyclo[2.2.1]heptan-2-yl]-5-methylpyrimidine-2,4(1H,3H)-dione (21) and after deprotection by transfer hydrogenation, free thymine analogue22. The thymine derivative21was converted to 2,3'-anhydronucleoside26. Treatment of the benzyl derivative18with sodium in liquid ammonia led to amine19, which was used as key intermediate for the construction of (1R*,2R*,3R*,4R*,5R*,6S*)-3-(6-chloro-9H-purin-9-yl)-6-(hydroxymethyl)-bicyclo[2.2.1]heptane-2,5-diol (28) and (1R*,2R*,3R*,4R*,5R*,6S*)-3-(2-amino-6-chloro-9H-purin-9-yl)-6-(hydroxymethyl)bicyclo[2.2.1]heptane-2,5-diol (33). Ammonolysis of28led to 6-amino-9H-purine derivative29. 6-(Dimethylamino)-9H-purine analogue30and 6-(cyclopropylamino)-9H-purine analogues31and34were prepared by aminolysis of corresponding chloropurine derivatives.

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13

Fun, Hoong-Kun, Ching Kheng Quah, Chengmei Huang, and Haitao Yu. "1-Benzyl-5-methoxy-2′,3-dimethyl-4,6-dioxa-2-azaspiro[bicyclo[3.2.0]hept-2-ene-7,4′-isoquinoline]-1′,3′(2′H,4′H)-dione." Acta Crystallographica Section E Structure Reports Online 67, no. 6 (May 7, 2011): o1311—o1312. http://dx.doi.org/10.1107/s160053681101600x.

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14

Scognamiglio, J., C. S. Letizia, and A. M. Api. "Fragrance material review on 1-[5(or 6)-methyl-7(or 8)-1-(methylethyl)bicyclo[2.2.2]oct-5-en-2-yl]ethan-1-one." Food and Chemical Toxicology 62 (December 2013): S61—S66. http://dx.doi.org/10.1016/j.fct.2013.08.066.

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15

Kim, JH, MJ Gallagher, and RF Toia. "Methanolysis of 4-Methyl-2,6,7-trioxa-1-phospha-bicyclo[2.2.2]octane 1-Oxide and 1-Sulfide: Mechanistic and Stereochemical Considerations." Australian Journal of Chemistry 47, no. 4 (1994): 715. http://dx.doi.org/10.1071/ch9940715.

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Methanolysis of 4-methyl-2,6,7-trioxa-1-phosphabicyclo[2.2.2]octane 1-oxide and 4-methyl-2,6,7- trioxa-1-phosphabicyclo[2.2.2]octane 1-sulfide have been studied by 31P n.m.r. spectroscopy. The trans-2-methoxy-5-methyl-1,3,2-dioxaphosphorinane-r-5-methanol 2-oxide and trans-2-methoxy-5-methyl-1,3,2-dioxaphosphorinane-r-5-methanol 2-sulfide are the initially formed products, respectively, but with time a product mixture comprising the trans- and cis -isomers and the acyclic dimethyl phosphate is formed. Methanolysis of the isolated trans-isomer, and of the isolated acyclic dimethyl phosphate under the same reaction conditions, suggests that the cis -isomer results from a recyclization reaction, rather than from the alternative ring opening of the bicyclic compound.

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16

Yang, Ying-Qun, Wei Li, Zhi-Min Chen, and Li-Xia Fu. "Crystal Structure and Properties of a New Copper(II) Complex Cu2(phen)2[C7H8(COO)2]2 (H2O)4:5." Zeitschrift für Naturforschung B 67, no. 9 (September 1, 2012): 872–76. http://dx.doi.org/10.5560/znb.2012-0097.

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A new complex Cu2(phen)2[C7H8(COO)2]2 (H2O)4:5 (1) has been synthesized, with the dianion of bicyclo[2.2.1] hept-2-ene-5,6-dicarboxylic acid [C7H8(COOH)2] (LH2) and 1,10-phenanthroline (phen) as ligands. In 1, L2- anions link Cu(II) cations to form two binuclear structure units, in which each Cu(II) cation is coordinated by five donor atoms to give a distorted square-pyramidal geometry. The magnetic data of 1 show that it exhibits weak antiferromagnetic properties at low temperature. When the excitation wavelength is at 470 nm, it has an intense photoluminescence. In addition, the cyclovoltammetric electron transfer is quasi reversible in the electrode reaction of 1, two electrons being involved in the reaction corresponding to Cu(II)=Cu(0)

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17

Kohl, Eva, Thomas Ströter, Christina Siedschlag, Kurt Polborn, and Günter Szeimies. "The Carbene/Bridgehead-Olefin Rearrangement: DFT Calculations on 1-Bicyclo[2.1.1]hexylcarbene and 1-Bicyclo[3.1.1]heptylcarbene; Rearrangement of (5-Bromobicyclo[3.1.1]heptyl)bromocarbene." European Journal of Organic Chemistry 1999, no. 11 (November 1999): 3057–66. http://dx.doi.org/10.1002/(sici)1099-0690(199911)1999:11<3057::aid-ejoc3057>3.0.co;2-m.

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18

MARUBAYASHI, Nobuhiro, Masami YAMASHITA, and Noriaki HIRAYAMA. "Crystal Structure of .ALPHA.-Bicyclo(2.2.1)hept-5-en-2-yl-.ALPHA.-phenyl-1-piperidinepropanol (Biperiden)." Analytical Sciences 15, no. 8 (1999): 815–16. http://dx.doi.org/10.2116/analsci.15.815.

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19

Goursolle, M., M. Bourhis, and A. H'Naïfi. "Structure du diéthylamino-1 éthyl-6 oxo-7 bicyclo[2.2.1]heptène-5 carboxylate-2 de méthyle." Acta Crystallographica Section C Crystal Structure Communications 42, no. 11 (November 15, 1986): 1641–42. http://dx.doi.org/10.1107/s0108270186091175.

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20

Gavina, Francisco, Ana M. Costero, Ana M. Gonzalez, and Santiago V. Luis. "Existence and reactivity of bicyclic annulenones. 2. Bicyclo[3.3.0]octa-1(5),3,7-triene-2,6-dione." Journal of Organic Chemistry 52, no. 14 (July 1987): 2997–99. http://dx.doi.org/10.1021/jo00390a009.

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21

Tănase, Drăghici, Hanganu, Pintilie, Maganu, Volobueva, Sinegubova, et al. "New HSV-1 Anti-Viral 1′-Homocarbocyclic Nucleoside Analogs with an Optically Active Substituted Bicyclo[2.2.1]Heptane Fragment as a Glycoside Moiety." Molecules 24, no. 13 (July 3, 2019): 2446. http://dx.doi.org/10.3390/molecules24132446.

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New 1′-homocarbanucleoside analogs with an optically active substituted bicyclo[2.2.1]heptane skeleton as sugar moiety were synthesized. The pyrimidine analogs with uracil, 5-fluorouracil, thymine and cytosine and key intermediate with 6-chloropurine (5) as nucleobases were synthesized by a selective Mitsunobu reaction on the primary hydroxymethyl group in the presence of 5-endo-hydroxyl group. Adenine and 6-substituted adenine homonucleosides were obtained by the substitution of the 6-chlorine atom of the key intermediate 5 with ammonia and selected amines, and 6-methoxy- and 6-ethoxy substituted purine homonucleosides by reaction with the corresponding alkoxides. No derivatives appeared active against entero, yellow fever, chikungunya, and adeno type 1viruses. Two compounds (6j and 6d) had lower IC50 (15 ± 2 and 21 ± 4 µM) and compound 6f had an identical value of IC50 (28 ± 4 µM) to that of acyclovir, suggesting that the bicyclo[2.2.1]heptane skeleton could be further studied to find a candidate for sugar moiety of the nucleosides.

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22

Dookhun, Veedeeta, and Andrew J. Bennet. "Synthesis and biological evaluation of a bicyclo[4.1.0]heptyl analogue of glucose-1-phosphate." Canadian Journal of Chemistry 82, no. 9 (September 1, 2004): 1361–64. http://dx.doi.org/10.1139/v04-109.

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The synthesis of a bicyclo[4.1.0]heptyl analogue of glucose-1-phophate, (1R,2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)-bicyclo[4.1.0]heptan-2-yl dihydrogen phosphate (5) is reported. The synthetic route chosen started with methyl α-D-glucopyranoside and was accomplished in 11 steps with an overall yield of 3%. Compound 5 was tested as a potential substrate of UTP:α-D-glucose-1-phosphate uridylyltransferase, the enzyme that converts glucose-1-phosphate into UDP-glucose. However, the conformationally restricted glucose-1-phosphate analogue 5 was found to be a weakly binding inhibitor, rather than a substrate, of the yeast transferase (12% inhibition at a concentration of 0.1 mmol L1).Key words: glucose 1-phosphate, inhibition, UTP:α-D-glucose-1-phosphate uridylyltransferase.

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23

Li, Qing, Dang Quan Zhang, Qi Mei Liu, and Kuan Peng. "Determination of Bioactive Components of 60°С Volatiles from Cinnamomum camphora Branches by TD-GC/MS." Advanced Materials Research 230-232 (May 2011): 852–56. http://dx.doi.org/10.4028/www.scientific.net/amr.230-232.852.

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The chemical components of helium volatiles from the fresh branches of Cinnamomum camphora were studied by TD-GC/MS. The analytical result by 60°С-based TD-GC/MS showed that 55 peaks were obtained from the helium volatiles from the fresh branches of Cinnamomum camphora and 53 chemical compounds were identified. The results showed that the main components were as: Bicyclo[2.2.1]heptan-2-one, 1,7,7-trimethyl-, (1R)- (15.4328%), 1,3-Benzodioxole, 5-(2-propenyl)- (14.881%), Tricyclo[2.2.1.0(2,6)]heptane, 1,7-dimethyl-7-(4-methyl-3-pentenyl)-, (-)- (12.694%), p-menth-1-en-8-ol (9.832%), Bicyclo[2.2.1]heptane, 2-methyl-3-methylene-2-(4-methyl-3- pentenyl)-, (1S-exo)- (6.143%), 1,6,10-Dodecatrien-3-ol, 3,7,11-trimethyl- (5.365%), Bicyclo[3.1.1] hept-2-ene, 2,6-dimethyl-6-(4-methyl-3-pentenyl)- (4.527%), Naphthalene, 1,2,3,5,6,8a- hexahydro-4,7-dimethyl-1-(1-methylethyl)-, (1S-cis)- (4.129%), 3-Cyclohexen-1-ol, 4-methyl-1- (1-methylethyl)- (2.965%), Borneol (2.627%), Bicyclo[2.2.1]heptan-2-ol, 1,7,7-trimethyl-, acetate, (1S-endo)- (2.586%), Copaene (2.534%), 1,6,10-Dodecatriene, 7,11-dimethyl-3-methylene-, (Z)- (1.612%), (-)-Isosativene (1.121%), etc. The analytical result suggested that the helium volatiles from the fresh branches of Cinnamomum camphora could be used as industrial materials of biomedicines and spicery.

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Shea, K. J., and L. D. Burke. "Bridgehead dienes. Thermal generation of the bicyclo[3.3.1]nona-1(2),4(5)-diene (ZZ) ring system." Tetrahedron Letters 28, no. 7 (January 1987): 735–38. http://dx.doi.org/10.1016/s0040-4039(01)80975-8.

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Koch, Ernst-Christian, and Guido J. Reiss. "Photochemisch induzierte C–C-Verknüpfungen zwischen einem Mangan-koordinierten Pentadienylliganden und Acetylen." Zeitschrift für Naturforschung B 70, no. 2 (February 1, 2015): 143–50. http://dx.doi.org/10.1515/znb-2014-0227.

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AbstractIrradiation of tricarbonyl(η5-2,4-dimethyl-2,4-pentadien-1-yl)manganese (1) in tetrahydrofuran (THF) at 208 K affords the carmine solvent complex dicarbonyl(η5-2,4-dimethyl-2,4-pentadien-1-yl)(THF)manganese (2). Complex 2 thermally reacts with acetylene (3) to give tricarbonyl(η3:2-1,3-dimethyl-bicyclo[3.3.1]-3,6-nonadien-2-yl)manganese (4) and dicarbonyl(5-7,10-13-η-6,8-dimethyl-1,3,5,8,10,12-tridecahexaen-5-yl)manganese (5). The crystal structure of complex 4 was determined at room temperature [triclinic space group $P\bar 1,$a=7.6891(9), b=8.3860(8), c=10.5252(13) Å, α=93.000(9)°, β=93.390(10)°, γ= 108.032(8)°, V=642.43(13) Å3]. The manganese atom is trigonal-bipyramidally coordinated by three carbonyl ligands, one ethenylic and one allylic fragment. Consequently, the bicyclic olefin ligand 1,3-dimethyl-bicyclo[3.3.1]-3,6-nonadiene coordinates the manganese atom in a η3:2 mode. The constitution of complex 5 was deduced from IR data, elemental analysis, and 1H NMR spectra. For the formation of complexes 4 and 5, a reaction mechanism is proposed.

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26

Moriguchi, Tetsuji, Suvratha Krishnamurthy, Toru Arai, Taisuke Matsumoto, Koji Araki, Akihiko Tsuge, and Norikazu Nishino. "Synthesis and Molecular Structure of tert-Butyl 3-oxo-2-oxa-5-azabicyclo[2.2.2]octane-5-carboxylate." Journal of Crystallography 2014 (August 17, 2014): 1–6. http://dx.doi.org/10.1155/2014/645079.

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The compound tert-butyl 3-oxo-2-oxa-5-azabicyclo[2.2.2]octane-5-carboxylate was synthesized as a cyclic amino acid ester from the corresponding ethyl 2-amino-4-(2-oxiranyl)butanoate HCl salt via an intramolecular lactonization reaction and was characterized by using 1H NMR spectroscopy and high-resolution mass spectrometry. The product was then recrystallized from dichloromethane/diethyl ether and its structure was determined via single crystal X-ray diffraction analysis. The crystal was found to be of the monoclinic space group P21/c (no. 14) with a = 10.217(2) Å, b = 11.676(3) Å, c = 10.273(3) Å, β = 114.186(13)°, and Dcalc = 1.350 g/cm3 at 123 K. The compound has bicyclo[2.2.2]octane structure including a lactone moiety and a piperidine ring, and the two diastereomers of the molecules are present in a 1 : 1 ratio in the crystal.

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27

Ngamga, Dieudonne, Josephine Bipa, Pearl Lebatha, Christabel Hiza, Joan Mutanyatta, Merha-Tibeb Bezabih, Pierre Tane, and Berhanu M. Abegaz. "Isoquinoline Alkaloids and Homoisoflavonoids from Drimiopsis barteri Bak and D. burkei Bak." Natural Product Communications 3, no. 5 (May 2008): 1934578X0800300. http://dx.doi.org/10.1177/1934578x0800300518.

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The powdered bulbs and leaves of Drimiopsis barteri yielded two novel isoquinoline alkaloids: 5-hydroxy-7,2′,3′,4′-tetramethoxy{2H-1-}benzopyran [4,3-c]isoquinoline and 6-hydroxy-7,2′,3′,4′-tetramethoxy{2H-1-}benzopyran [4,3-c]isoquinoline, three new scillascillins: 5,7-dihydroxy-2′,3′,4′-trimethoxyspiro-{2H-1-benzopyran-7′-bicyclo [4.2.0]octa[1,3,5]-triene}-4-one, 5-hydroxy-7,2′,3′,4′-tetramethoxyspiro{2H-1-benzopyran-7′-bicyclo [4.2.0]octa[1,3,5]-triene}-4-one and 5,2′,4′-trihydroxy-7,3′-dimethoxyspiro{2H-1-benzopyran-7′-bicyclo [4.2.0]octa[1,3,5]-triene}-4-one, and a tetrahydroxyhomo-isoflavanone: 5,6,7-trihydroxy-3-(4-hydroxybenzyl)chroman-4-one. The bulbs of Drimiopsis burkei gave three new metabolites: the first scillascillin, mentioned above, and two xanthones: 1,6-dihydroxy-2,3-dimethoxy-8-methylxanthone and 1,4-dihydroxy-2,3,6-trimethoxy-8-methylxanthone. Seventeen known compounds were isolated from both plants. Structures were elucidated based on detailed 1-, and 2D-NMR spectroscopic and MS analyses.

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28

Weber, Martin, Gábor Balázs, Alexander V. Virovets, Eugenia Peresypkina, and Manfred Scheer. "Insertion of Phosphenium Ions into a Bicyclo[1.1.0]Tetraphosphabutane Iron Complex." Molecules 26, no. 13 (June 26, 2021): 3920. http://dx.doi.org/10.3390/molecules26133920.

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By reacting [{Cp‴Fe(CO)2}2(µ,η1:1-P4)] (1) with in situ generated phosphenium ions [Ph2P][A] ([A]− = [OTf]− = [O3SCF3]−, [PF6]−), a mixture of two main products of the composition [{Cp‴Fe(CO)2}2(µ,η1:1-P5(C6H5)2)][PF6] (2a and 3a) could be identified by extensive 31P NMR spectroscopic studies at 193 K. Compound 3a was also characterized by X-ray diffraction analysis, showing the rarely observed bicyclo[2.1.0]pentaphosphapentane unit. At room temperature, the novel compound [{Cp‴Fe}(µ,η4:1-P5Ph2){Cp‴(CO)2Fe}][PF6] (4) is formed by decarbonylation. Reacting 1 with in situ generated diphenyl arsenium ions gives short-lived intermediates at 193 K which disproportionate at room temperature into tetraphenyldiarsine and [{Cp‴Fe(CO)2}4(µ4,η1:1:1:1-P8)][OTf]2 (5) containing a tetracyclo[3.3.0.02,7.03,6]octaphosphaoctane ligand.

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29

Peng, Wan Xi, Qiu Xue, Feng Juan Wu, Xu Zhang, and Zhong Feng Zhang. "Analysis on Health Risk of Volatile Organic Compounds of Smoked Bamboo Biomaterial by TD-GC-MS." Key Engineering Materials 467-469 (February 2011): 1697–701. http://dx.doi.org/10.4028/www.scientific.net/kem.467-469.1697.

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Smoked bamboo, which was made by bamboo in high temperature smoke, is a new indoors materials. In order to evaluate its potential health risk to human settlements, the volatile organic compounds of smoked bamboo biomaterial were adsorbed and determined by TD-GC-MS. And the main constituents of volatiles at 60°С were cyclononasiloxane, octadecamethyl-(35.14%), acetic acid(23.27%), cyclotrisiloxane, hexamethyl- (9.53%), bicyclo[4.4.0]dec-1-ene,2-isoprop yl-5-methyl-9-methylene-(7.56%), silane, 1,4-phenylenebis[trimethyl(4.32%), 1,3-benzodioxole, 5-(2-propenyl)- (3.47%), cedrol(2.75%), etc. (2) The main constituents of volatiles at 130°С were acetic acid(43.78%), 2,5-furandione, dihydro-3- methylene-(16.57%), 1,3-benzodioxole, 5-(1-propenyl)-,(z)-(6.75%), octasiloxane, 1,1,3,3,5,5,7,7,9,9, 11,11,13, 13,15,15- hexadecamethyl -(4.09%), bicyclo[2.2.1]heptan-2-one, 1,7,7- trimethyl-, (1s)- (3.21%), etc. Generally, the smoked bamboo biomaterial was safe under 60-130°С.

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30

Fun, Hoong-Kun, Ching Kheng Quah, Chengmei Huang, and Haitao Yu. "5-Methoxy-1,2′,3-trimethyl-4,6-dioxa-2-azaspiro[bicyclo[3.2.0]hept-2-ene-7,4′-isoquinoline]-1′,3′(2′H,4′H)-dione." Acta Crystallographica Section E Structure Reports Online 67, no. 6 (May 7, 2011): o1340—o1341. http://dx.doi.org/10.1107/s1600536811016266.

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31

Ma, Qing Zhi, Feng Juan Wu¨, Dang Quan Zhang, and Wan Xi Peng. "Analysis on Function Components and Biohealth Function of Phyllostachys heterocycla Biomass." Advanced Materials Research 129-131 (August 2010): 55–59. http://dx.doi.org/10.4028/www.scientific.net/amr.129-131.55.

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Phyllostachys heterocycla, who was considered to have biohealth function in folk, is becoming a major biomass in rooms. Therefore, the chemical components from Phyllostachys heterocycla were identified by TD-GC/MS at different temperature. The main function components of Phyllostachys heterocycla biomass at 40°С were 1,2-benzenedicarboxylic acid, mono(2-ethylhexyl) ester(21.32%), [1,1':3',1''-terphenyl]-2'-ol(9.16%), (2,3-diphenylcyclopropyl)methyl ph enyl sulfoxide, trans-(6.54%), cedrol(6.11%), bicyclo[2.2.1]heptan-2-one, 1,7,7- trimethyl-, (1r)- (6.04%), 1,6-cyclodecadiene, 1-methyl-5-met hylene-8-(1-methylethyl)- (4.82%), 1-heptadecanamine(4.79%), propanedioic acid, methyl-, diethy l ester(4.36%), squalene(4.25%), etc. And the main function components at 60°С were1,2-benzenedicarboxylic acid, mono(2-ethylhexyl) ester(14.02%), camphor(10.57%), [1,1':3',1''-terphenyl]-2'-ol(6.91%), pentanoic acid, 2-benzenmethanimin yl-5-guanidinyl-(5.68%), 1,6-cyclodecadiene, 1-methyl-5-methyl- (5.27%), cedrol(4.83%), 2-bromo-2,2-dichloroethylcarbamic acid, ethyl ester(4.56%), n-n-butylpropionamide(4.49%), bicyclo[3.1.1]heptane, 6,6-dimethy l-2-methylene-, (1s)- (4.12%), etc. Phyllostachys heterocycla biomass was more healthy to human at 40°С than 60°С. So Phyllostachys heterocycla biomass was fit to use after drying.

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32

KATAYAMA, Sadamu, Hajime HIRAMATSU, Keiichi AOE, and Masashige YAMAUCHI. "Synthesis of 1-Hydroxybicyclo(3.2.1)oct-3-en-2-ones by Acyloin Rearrangement of 1-Methoxy- or 1-tert-Butyldimethylsilyloxy-bicyclo(2.2.2)oct-5-en-2-ones." CHEMICAL & PHARMACEUTICAL BULLETIN 45, no. 9 (1997): 1419–27. http://dx.doi.org/10.1248/cpb.45.1419.

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33

Fun, Hoong-Kun, Ching Kheng Quah, Chengmei Huang, and Haitao Yu. "(1S*,4′S*,5R*)-1-Isopropyl-5-methoxy-2′,3-dimethyl-4,6-dioxa-2-azaspiro[bicyclo[3.2.0]hept-2-ene-7,4′-isoquinoline]-1′,3′(2′H,4′H)-dione." Acta Crystallographica Section E Structure Reports Online 67, no. 5 (April 29, 2011): o1271—o1272. http://dx.doi.org/10.1107/s1600536811015315.

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34

Fun, Hoong-Kun, Ching Kheng Quah, Chengmei Huang, and Haitao Yu. "(1S*,4′S*,5R*)-1-Isobutyl-5-methoxy-2′,3-dimethyl-4,6-dioxa-2-azaspiro[bicyclo[3.2.0]hept-2-ene-7,4′-isoquinoline]-1′,3′(2′H,4′H)-dione." Acta Crystallographica Section E Structure Reports Online 67, no. 5 (April 29, 2011): o1273—o1274. http://dx.doi.org/10.1107/s1600536811015327.

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35

Min, Long, Xin Liu, and Chuang-Chuang Li. "Total Synthesis of Natural Products with Bridged Bicyclo[m.n.1] Ring Systems via Type II [5 + 2] Cycloaddition." Accounts of Chemical Research 53, no. 3 (February 18, 2020): 703–18. http://dx.doi.org/10.1021/acs.accounts.9b00640.

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36

Kurzer, Frederick, and Jane E. Hawkes. "Bicyclo[2.2.2]octane-2-spirocyclohexanes, Part 5 [1] The Action of Grignard Reagents on Spirodiisophora-3′,6-dione." Zeitschrift für Naturforschung B 47, no. 7 (July 1, 1992): 1000–1006. http://dx.doi.org/10.1515/znb-1992-0718.

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Grignard reagents react with spirodiisophora-3′,6-dione exclusively at its 3′-keto-function, yielding 3′-eq-alkyl(or phenyl)-3′-ax-hydroxyspirodiisophor-6-ones. Successive dehydration and monobromination of the methyl homologue yields products, the structural details of which are settled by their 13C NMR spectra.

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37

KUZNETSOV, M. A., I. D. KUCHUK, and V. A. GINDIN. "ChemInform Abstract: Thermolysis and Photolysis of 4,4,6,6-Tetramethyl-1-phenyl-5-phenylethynyl-2,3-diaza-2-bicyclo [3.1.0]hexene." ChemInform 29, no. 32 (June 20, 2010): no. http://dx.doi.org/10.1002/chin.199832059.

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38

Brown, RFC, KJ Coulston, FW Eastwood, ADE Pullin, and AC Staffa. "Argon Matrix Study of the Infrared Spectrum of Butatrienone." Australian Journal of Chemistry 43, no. 3 (1990): 561. http://dx.doi.org/10.1071/ch9900561.

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Butatrienone, H2C=C=C=C=O, was generated by pyrolysis of each of six different precursors in a stream of argon at temperatures in the range 710-880°C, and the pyrolysate-argon mixture was condensed on a Csl plate at c. 10 K. Infrared spectra were obtained between 4000 and 250 cm-1. Two precursors, buta-2,3-dienoic trifluoracetic anhydride (1) and buta-2,3-dienoyl chloride (2), gave pyrolysates showing a spectrum consisting of six strong bands and five weak bands. Four precursors, bicyclo [2.2.1]hept-5′-en-2′-ylideneacetic trifluoracetic anhydride (3), 5-( bicyclo [2.2.1]hept-5′-en-2′-ylidene)-2,2-dimethyl-1,3-dioxan-4,6- dione (4),2,2-dimethyl-5-(7?-oxabicyclo[2.2.1]hept-5?-en-2?-ylidene)- 1,3-dioxan-4,6-dione (5) and 3,4-diazatricyclo[5.2.1.02,6]deca-3,8-diene-endo-cis-2,6-dicarboxylic anhydride (6) gave pyrolysates showing spectra consisting principally of the six strong bands. The observed bands assigned to matrix-isolated butatrienone were at 3105w, 3035s, 3010w, 2964w, 2242s, 1996w, 1495s, 1456s, 728s, 404w cm-1. Calculated frequencies, using various models, for butatrienone are reported and are used to make plausible assignments. The strongest band (v2) attributed to butatrienone was at 2242 cm-1 which was shifted to 2200 cm-1 in (1-13C) butatrienone.

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39

Buzas, Andrea, and Fabien Gagosz. "Gold(I) Catalyzed Isomerization of 5-en-2-yn-1-yl Acetates: An Efficient Access to Acetoxy Bicyclo[3.1.0]hexenes and 2-Cycloalken-1-ones." Journal of the American Chemical Society 128, no. 39 (October 2006): 12614–15. http://dx.doi.org/10.1021/ja064223m.

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40

Freeman, Fillmore, Mark Y. Lee, Hengyao Lu, Xiaojing Wang, and Eloy Rodriguez. "1-Thia-Cope Rearrangements during the Thionation of 2-endo-3-endo-Bis(aroyl)bicyclo[2.2.1]hept-5-enes." Journal of Organic Chemistry 59, no. 13 (July 1994): 3695–98. http://dx.doi.org/10.1021/jo00092a034.

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41

KATAYAMA, S., H. HIRAMATSU, K. AOE, and M. YAMAUCHI. "ChemInform Abstract: Synthesis of 1-Hydroxybicyclo[3.2.1]oct-3-en-2-ones by Acyloin Rearrangement of 1-Methoxy- or 1-tert-Butyldimethylsilyloxy-bicyclo[2.2.2]oct-5-en-2-ones." ChemInform 29, no. 11 (June 23, 2010): no. http://dx.doi.org/10.1002/chin.199811102.

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42

Werstiuk, Nick Henry, and Jiangong Ma. "Applications and evaluation of IGAIM 13C and 1H chemical shift calculations for unsaturated hydrocarbons and organolithium compounds." Canadian Journal of Chemistry 74, no. 6 (June 1, 1996): 875–84. http://dx.doi.org/10.1139/v96-096.

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Wave functions obtained at the RHF/6-31+G(d) level of theory were used with the new method IGAIM (individual gauges for atoms in molecules) developed by Keith and Bader to calculate the isotropic 13C and 1H NMR chemical shifts of a group of neutral molecules (bicyclo[3.2.1]octa-2,6-diene (1), bicyclo[3.2.1]oct-6-ene (2), bicyclo[2.2.1]hepta-2,5-diene (3), benzene (4)), carbanions (prop-2-en-1-yl (allyl) (5), bicyclo[3.2.1]octa-3,6-dien-2-yl (8)), and lithium complexes (prop-2-en-1-yllithium (6) and its dimer 7, bicyclo[3.2.1]octa-3,6-dien-2-yllithium (9)). The theoretical isotropic 13C NMR chemical shifts of the neutral molecules, relative to the calculated value for TMS(tetramethylsilane), are in excellent agreement with the experimental values, with differences between the sets of data ranging from +4.9 to −7.1 ppm. For the same group of compounds the theoretical 1H shifts are lower than the experimental values by increments ranging between 0.4 and 1.29 ppm. For allyllithium, which exists as an unsymmetrical fluxional dimer, the theoretical averaged 13C shifts are larger, 2.6 ppm for the terminal carbons and 16.7 ppm for the central carbon, than the experimental values. In the case of 8, originally considered to be a bishomoaromatic species, the theoretical 13C chemical shifts of its Li+ complex 9 differ from the experimental ones for THF-solvated 9 by values that range from +6.2 to −15.0 ppm. Yet, the relative theoretical chemical shifts — of special importance is the fact that the carbons of the vinylene bridge of this compound are unusually shielded relative to the parent diene 1 — correlate with the experimental data. The 1H chemical shifts calculated for the hydrocarbons 1, 2, 3, 4 and the lithium complexes 7 and 9 range from 0.08 to 1.38 ppm less than the experimental values. To gain information on whether variations in charge density play a significant role in determining the magnitudes of the chemical shifts, we used AIMPAC calculations to obtain the atom electron populations of diene 1, 5, 6, dimer 7, 8, and 9. We find no obvious correlation between the charges on the carbon atoms and the 13shifts for this set of compounds. Key words: IGAIM, calculations, 13C and 1H chemical shifts, unsaturated hydrocarbons, organolithium compounds.

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43

Chan, Isa Y. H., Mohan M. Bhadbhade, and Roger Bishop. "Threefold helical assembly via hydroxy hydrogen bonds: the 2:1 co-crystal of bicyclo[3.3.0]octane-endo-3,endo-7-diol and bicyclo[3.3.0]octane-endo-3,exo-7-diol." Acta Crystallographica Section E Crystallographic Communications 77, no. 3 (February 19, 2021): 270–76. http://dx.doi.org/10.1107/s2056989021001730.

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Reduction of bicyclo[3.3.0]octane-3,7-dione yields a mixture of the endo-3,endo-7-diol and endo-3, exo-7-diol (C8H14O2) isomers (5 and 6). These form (5)2·(6) co-crystals in the monoclinic P21/n space group (with Z = 6, Z′ = 1.5) rather than undergoing separation by means of fractional recrystallization or column chromatography. The molecule of 5 occupies a general position, whereas the molecule of 6 is disordered over two orientations across a centre of symmetry with occupancies of 0.463 (2) and 0.037 (2). Individual diol hydroxy groups associate around a pseudo-threefold screw axis by means of hydrogen bonding. The second hydroxy group of each diol behaves in a similar manner, generating a three-dimensional hydrogen-bonded network structure. This hydrogen-bond connectivity is identical to that present in three known helical tubuland diol–hydroquinone co-crystals, and the new crystal structure is even more similar to two homologous aliphatic diol co-crystals.

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44

Reza Salari, Mohammad, Mohammad H. Mosslemin, and Alireza Hassanabadi. "Green synthesis of trans-(4-chlorophenyl)-7-aryl-6,7-dihydro[1,3]dioxolo[4,5-f][1]benzofuran-6-yl)methanones in an aqueous medium." Journal of Chemical Research 43, no. 3-4 (March 2019): 86–89. http://dx.doi.org/10.1177/1747519819836527.

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A three-component one-pot condensation of 2-[2-(4-chlorophenyl)-2-oxoethyl)]isoquinolinium bromide with benzo[1,3]dioxol-5-ol and an arylglyoxal in the presence of catalytic amounts of 1,4-diaza-bicyclo[2.2.2]octane in refluxing water gave a series of seven trans-(4-chlorophenyl)-7-aryl-6,7-dihydro[1,3]dioxolo[4,5- f][1]benzofuran-6-yl)methanones in excellent yield and in a short time.

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45

Maas, Gerhard, and Rainer Rahm. "A Proton-Catalyzed Dimerization of a 2-Amino-1,3-diene which Ultimately Yields a 3-Aminobicyclo[4.2.0]octa-2,4-diene." Zeitschrift für Naturforschung B 60, no. 6 (June 1, 2005): 673–76. http://dx.doi.org/10.1515/znb-2005-0611.

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The 2-pyrrolidino-1,3-dienes (E)-5 and (Z)-5 are obtained by the reaction of lithium di(tertbutyl) cuprate with propyne iminium salt 3. Quantitative Z→E isomerization of 5 takes place within 4 hours at 20 °C. In benzene solution, (E)-5 slowly equilibrates with a [1,5]-H shift to form the 1-amino-1,3-diene derivative 6. In concentrated chloroform solution, however, (E)-5 is transformed into the 3-pyrrolidino-bicyclo[4.2.0]octa-2,4-diene 7 which is identified by X-ray crystal structure analysis. A mechanism for this transformation is proposed.

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46

Kreiter, Cornelius G., and Klaus Lehr. "Photochemische Reaktionen von Übergangsmetall-Organyl-Komplexen mit Olefnen, VI. Reaktionen von Tricarbonyl-η5-2,4-cyclohexadienyl-mangan mit konjugierten Dienen / Photochemical Reactions of Transition Metal Organyl Complexes with Olefins, VI. Reactions of Tricarbonyl (η5-2,4-cyclohexadienyl)manganese with Conjugated Dienes." Zeitschrift für Naturforschung B 46, no. 10 (October 1, 1991): 1377–83. http://dx.doi.org/10.1515/znb-1991-1016.

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Tricarbonyl-η5-2,4-cyclohexadien-1-yl-manganese (1) was reacted photochemically at 253 K with simple conjugated dienes. Four different types of products were obtained, depending upon the dienes. With 1,3-butadiene (A) dicarbonyl-η4:3-1-(3-buten-1,2-diyl)-2,4-cyclohexadiene-manganese (2A) is isolated. 2-Methyl-1,3-butadiene (B) yields the methyl-substituted diastereomeric dicarbonyls 2B, 2B′, the [4+5]-cycloadduct tricarbonyl-η3:2-3-methyl-bicyclo-[4.3.1]-3,8-decadien-7-yl-manganese (3B) and tetracarbonyl-η3-4-methylene-bicyclo[4.3.1]-8-decen-3-yl-manganese (4B) with an exocyclically coordinated tetracarbonylmanganese fragment. With 2,3-dimethyl-1,3-butadiene (C) only the [4+5]-cycloadduct 3C and the tetracarbonyl 4C are obtained. No CC-bond formation is observed with E,E-2,4-hexadiene (D) and 1,3-cyclohexadiene (E). Carbonyl-η5-2,4-cyclohexadien-1 -yl-η4-E,E-2,4-hexadiene-manganese (5D), and carbonyl-η4-1,3-cyclohexadiene-η5-2,4-cyclohexadien-1-yl-manganese (5E) are the only products. The complexes were separated and purified by HPL chromatography. Their constitutions were determined by IR and NMR spectroscopy.

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47

Lin', Ji-Mao, Li Fang, and Wen-Tao Huang. "Synthesis of γ-N-[(Arylideneaminoethyl)-Aminoethyl]Aminopropyl-2, 8, 9-Trioxa-5-aza-1-sila-bicyclo[3, 3, 3]undecanes." Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry 25, no. 9 (November 1995): 1467–77. http://dx.doi.org/10.1080/15533179508218283.

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48

Pal’chikov, V. A., S. A. Prid’ma, and L. I. Kas’yan. "Synthesis and aminolysis of N-(bicyclo[2.2.1]hept-5-en-endo-2-ylmethyl)-N-(oxiran-2-ylmethyl)(7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonamide." Russian Journal of Organic Chemistry 50, no. 9 (September 2014): 1312–16. http://dx.doi.org/10.1134/s1070428014090139.

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49

Werstiuk, Nick Henry, and Jiangong Ma. "An ab initio study on the magnetic susceptibility and magnetically induced current density distribution of the bicyclo[3.2.1]octa-3,6-dien-2-yl anion." Canadian Journal of Chemistry 77, no. 5-6 (June 1, 1999): 752–59. http://dx.doi.org/10.1139/v99-049.

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The molecular susceptibility and the atomic contributions including the basin and surface components calculated at the RHF/6-31+G(d)//6-31+G(d) level of theory along with vector current densities obtained at the 6-31++G(d,p)//6-31+G(d) and 6-31+G(d)//6-31+G(d) levels are reported for benzene (1) and correlated - the agreement is excellent - with the results obtained by Keith and Bader with the 6-311++G(2d,2p) basis. This validates our similar studies on the bicyclo[3.2.1]octa-3,6-dien-2-yl anion (2) - initially considered to be a bishomoaromatic species - its parent hydrocarbon bicyclo[3.2.1]octa-2,5-diene (3), the bicyclo[3.2.1]oct-3-ene-2-yl anion (4), and 5, the lithium complex of 2. While a magnetic susceptibility exhalation is found in going from 4 to 2, the increase in atomic surface contribution to Δχ arises predominately (42.6%) from the ethenyl bridge carbons C6 and C7, with C2 + C4 and C3 exhibiting substantially smaller increases (27.4 and 8.3%, respectively). This result, in conjunction with the nature of the vector current density maps of 2 and 4, provides further evidence that 2 does not possess a ring current as depicted in 2-bh, the usual representation of "bishomoaromatic" 2.Key words: ab initio calculations, IGAIM, CSGT, magnetic susceptibility, induced current density distributions, bicyclo[3.2.1]octa-3,6-dien-2-yl anion.

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Klunder, A. J. H., F. J. C. Van Gastel, J. M. M. Smits, Paul T. Beurskens, and Gezina Beurskens. "Crystal and molecular structure of (2R,3R)-2-exo-((1R)-1-hydroxy-2-methyl-propyl)-3-exo-hydroxymethyl-bicyclo[2.2.1]-hept-5-ene, C12H20O2." Journal of Chemical Crystallography 25, no. 7 (July 1995): 389–92. http://dx.doi.org/10.1007/bf01665275.

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