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Journal articles on the topic 'Bicyclo[3'

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Published: 4 June 2021

Last updated: 2 February 2022

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1

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 (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-acetoxyacrylon

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2

Chen, Shi Peng, Jian Ting Zhang, Dong Wang Liu, et al. "A Prophase Study on Applying Conia-Ene Reation in Constructing bicyclo [3, 3, 1] Nonane Ring." Advanced Materials Research 781-784 (September 2013): 1172–74. http://dx.doi.org/10.4028/www.scientific.net/amr.781-784.1172.

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The bicyclo [3, 3, 1] nonane ring system is the main structural feature in the lycopodium alkaloids. There are many methods to build the [3, 3, 1] bridged ring system, Herein, we designed to use indium Lewis acid which can activate the triple bond to construct [3, 3, 1] bridged ring system via Conia-ene reaction, and described a prophase study of applying Conia-ene reaction to construct such bicycle [3, 3, 1] nonane ring.

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3

Binder, Herbert, Walter Matheis, Gernot Heckmann, Hans-Jörg Deiseroth та Han Fu-Son. "Über bicyclische Diacyloxy-pentafluoro-μ3-oxotriborane 2.2.6.10.10-Pentafluoro-4.8-dialkyl-1.3.5.7.9-pentaoxa-2.6.10-triborabicyclo(4.4.0)decadiene: Darstellung, Molekül- und Kristallstruktur". Zeitschrift für Naturforschung B 40, № 7 (1985): 934–41. http://dx.doi.org/10.1515/znb-1985-0715.

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Abstract Bicyclic acyloxyfluoroboranes 3 react with BF3 by an insertion reaction to form bicyclic diacyloxy- pentafluoro-μ3-oxotriboranes of the 2.2.6.10.10-pentafluoro-4.8-dialkyl-1.3.5.7.9-pentaoxa- 2.6.10-tribora-bicyclo(4.4.0)decadiene type 4. A X-ray crystal structure determination of 4b is reported. NM R data of 4b in the solid state and in solution are discussed.

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4

Hřebabecký, Hubert, Milena Masojídková, and Antonín Holý. "Synthesis of Novel Conformationally Locked Carbocyclic Nucleosides Derived from 5,5- and 6,6-Bis(hydroxymethyl)bicyclo[2.2.1]heptan-2-ol." Collection of Czechoslovak Chemical Communications 70, no. 4 (2005): 519–38. http://dx.doi.org/10.1135/cccc20050519.

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(1R*,2R*,3R*,4S*)-3-Amino-6,6-bis(hydroxymethyl)bicyclo[2.2.1]heptan-2-ol (13) was prepared from (bicyclo[2.2.1]hept-5-ene-2,2-diyl)dimethyl dibenzoate (7) viacis-diol8, cyclic sulfate10, and azide12. (1R*,2R*,3S*,4S*)-3-Amino-6,6-bis(hydroxymethyl)bicyclo[2.2.1]-heptan-2-ol (18) and (1R*,2S*,3S*,4S*)-3-amino-5,5-bis(hydroxymethyl)bicyclo[2.2.1]heptan-2-ol (19) were obtained by addition of chromyl azide to double bond of7, chromatographic separation, debenzoylation and hydrogenation of resulting azides14and16. The amines13,18, and19were used to build (1R*,2R*,3R*,4S*)- (21a), (1R*,2R*,3S*,4S*)

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5

YAMAMOTO, T., T. EKI, S. NAGUMO, H. SUEMUNE, and K. SAKAI. "ChemInform Abstract: Novel Skeletal Transformation of Bicyclo(3.3.0)octanones to Bicyclo(3. 2.1)octenes." ChemInform 22, no. 50 (2010): no. http://dx.doi.org/10.1002/chin.199150080.

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6

Zhu, Fang-Hua, Jun-Xiao Yang, Zhi-Hua Mao, and Ru-Gang Xie. "1-[Bicyclo[4.2.0]octa-1(6),2,4-trien-3-yl]-3-[bicyclo[4.2.0]octa-1(6),2,4-trien-3-ylmethyl]imidazolium hexafluorophosphate." Acta Crystallographica Section E Structure Reports Online 64, no. 2 (2008): o434. http://dx.doi.org/10.1107/s1600536807067086.

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7

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 d

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8

Liu, Qi Mei, та Wan Xi Peng. "80°С-Based TD-GC/MS Analysis of Chemical Components from Branches of Cinnamomum camphora". Key Engineering Materials 480-481 (червень 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

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9

Loughlin, Wendy A. "A Facile Approach to Bicyclo[n.2.0]alkan-1-ols: An Overview." Australian Journal of Chemistry 57, no. 4 (2004): 335. http://dx.doi.org/10.1071/ch03213.

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Bicyclo[n.2.0]alkan-1-ols are an integral part of various frameworks of natural products. The reaction of the lithium enolates of simple ketones with (±)-phenyl vinyl sulfoxide and the controlled formation of bicyclo[n.2.0]alkan-1-ols was investigated. Facile access to bicyclo[n.2.0]alkan-1-ols (n = 3–6) bearing a bridgehead hydroxyl group was obtained. The ratio of bicyclo[n.2.0]alkan-1-ols (n = 3–6) to alkyated ketone was found to be dependent on enolate reactivity, electrophile conversion, time, reaction temperature, concentration, as well as the stability and steric strain observed in the

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10

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 (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 (

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11

Özlügedik, Mustafa, Seda Ünaldi, Birgit Wibbeling, and Dieter Hoppe. "Synthesis of Enantioenrichedtrans-Fused Bicyclo[4.4.0]- dec-3-enes and Bicyclo[4.3.0]non-3-enes Bearing a 1,5-Lactone Bridge." Advanced Synthesis & Catalysis 347, no. 11-13 (2005): 1627–31. http://dx.doi.org/10.1002/adsc.200505143.

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12

Hřebabecký, Hubert, Martin Dračínský, and Antonín Holý. "Synthesis of Novel Carbocyclic Nucleoside Analogues Containing Bicyclo[2.2.1]hept-2-ene-2-methanol." Collection of Czechoslovak Chemical Communications 73, no. 1 (2008): 44–58. http://dx.doi.org/10.1135/cccc20080044.

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Starting ethyl (1R*,2R*,3R*,4S*)-3-bromobicyclo[2.2.1]hept-5-ene-2-carboxylate (9) was reduced with LiAlH4and benzoylated giving [(1R*,2R*,3R*,4S*)-3-bromobicyclo[2.2.1]hept-5-en-2-yl]methyl benzoate (11). Treatment of11with NaN3and CrO3in acetic acid afforded [(1R*,2S*,3R*,4R*,5S*,6R*)-6-azido-3-bromo-5-hydroxybicyclo[2.2.1]hept-2-yl]methyl benzoate (12a) and [(1R*,2S*,3S*,4R*,5S*,6R*)-5-azido-3-bromo-6-hydroxybicyclo[2.2.1]heptan-2-yl]-methyl benzoate (12b). These key intermediates were separated and converted in five reaction steps to (1R*,2R*,3S*,4S*)-3-[(5-amino-6-chloropyrimidin-4-yl)ami

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13

Zaytsev, Andrey V., James E. Pickles, Suzannah J. Harnor, et al. "Concise syntheses of bridged morpholines." RSC Advances 6, no. 59 (2016): 53955–57. http://dx.doi.org/10.1039/c6ra08737j.

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Practical syntheses of 8-oxa-3-aza-bicyclo[3.2.1]octane and 9-oxa-3-aza-bicyclo[3.3.1]nonane, useful intermediates for synthesising kinase inhibitors, were achieved from readily available starting materials, using a solvent-free thermolytic cyclisation for the key step.

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14

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 (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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15

Yates, Peter, Rupinder S. Grewal, Peter C. Hayes, and Jeffery F. Sawyer. "Synthesis of cedranoid sesquiterpenes. V. The biotols." Canadian Journal of Chemistry 66, no. 11 (1988): 2805–15. http://dx.doi.org/10.1139/v88-434.

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Reduction of dimethyl 3-hydroxy-4,4,8-trimethyl-6-oxo-cis-bicyclo[3.3.0]octa-2,7-diene-1,2-dicarboxylate (8) with lithium and ammonia gives dimethyl 3-hydroxy-4,4,exo-8-trimethyl-6-oxo-cis-bicyclo[3.3.0]oct-2-ene-1,2-dicarboxylate (9), which on acetylation, reduction with sodium borohydride, and methanolysis gives dimethyl 3,exo-6-dihydroxy-4,4,exo-8-trimethyl-cis-bicyclo[3.3.0]oct-2-ene-1,2-dicarboxylate (12). This on 2-decarbomethoxylation followed by treatment with lithium acetylide in the presence of cerium trichloride gives methyl 3-ethynyl-3,exo-6-dihydroxy-4,4,exo-8-trimethyl-cis-bicycl

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16

Sonar, Vijayakumar N., Sean Parkin, and Peter A. Crooks. "(Z)-2-Thiophen-3-ylmethylene-1-aza-bicyclo[2.2.2]octan-3-one." Acta Crystallographica Section E Structure Reports Online 59, no. 10 (2003): o1464—o1466. http://dx.doi.org/10.1107/s1600536803019007.

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17

Manuel, G., A. Faucher, and P. Mazerolles. "Thia-6 diphényl-3,3 sila-3 (et germa-3)bicyclo[3.1.0]hexanes." Journal of Organometallic Chemistry 327, no. 2 (1987): C25—C28. http://dx.doi.org/10.1016/0022-328x(87)80212-7.

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18

Piers, Edward, Grace L. Jung, and Edward H. Ruediger. "Synthesis of functionalized bicyclo[3.2.1]octa-2,6-dienes by thermal rearrangement of substituted 6-exo-(1-alkenyl)bicyclo[3.1.0]hex-2-ene systems." Canadian Journal of Chemistry 65, no. 3 (1987): 670–82. http://dx.doi.org/10.1139/v87-115.

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Thermolysis of each of the enol silyl ethers 31–35 affords, cleanly and efficiently, the bicyclo[3.2.1]octadienes 36–40, respectively. Similarly, thermal rearrangement of the enol silyl ether 50 provides the diene 51. Hydrolysis of 36, 37, and 39, and decarbomethoxylation of the resultant keto esters 41, 42, and 44, gives the ketones 46–48, respectively. The ketone 46 is also obtained by acid hydrolysis of 51. Conversion of 6-methyl-1-hepten-4-yn-3-ol (56) into the enol ether 63 is described. Thermolysis of 63 gives 64, which, upon acid hydrolysis, affords 65. Thermolysis of the enones 68 and

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19

Gray, Brian D., Catherine M. McMillan, J. Allen Miller, and Michael Moore. "Bicyclo[3.2.1]oct-6-enes via (3+2)cycloaddition." Tetrahedron Letters 28, no. 2 (1987): 235–38. http://dx.doi.org/10.1016/s0040-4039(00)95695-8.

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20

Michaelides, Iacovos N., Benjamin Darses, and Darren J. Dixon. "Acid-Catalyzed Synthesis of Bicyclo[3.n.1]alkenediones." Organic Letters 13, no. 4 (2011): 664–67. http://dx.doi.org/10.1021/ol102909t.

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21

Novakov, I. A., B. S. Orlinson, R. V. Brunilin, A. A. Bakshaeva, and E. V. Sorokina. "Synthesis of 2-(Aminoalkyl)-3-(aminophenyl)bicyclo[2.2.1]heptanes." Russian Journal of General Chemistry 85, no. 3 (2015): 761–63. http://dx.doi.org/10.1134/s1070363215030378.

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22

Jin, Song, Norbert G. Swoboda-Colberg, and Patricia J. S. Colberg. "Microbial degradation of quadricyclane-derived tricyclo[2.2.1.02,6]heptan-3-ol in soil." Canadian Journal of Microbiology 43, no. 3 (1997): 300–303. http://dx.doi.org/10.1139/m97-042.

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Quadricyclane (tetracyclo[3.2.02,7.04,6]heptane) is a strained, saturated cyclic hydrocarbon and a potential environmental contaminant because of uses in solar energy and optical memory storage devices and as a recently proposed additive to jet fuel. Quadricyclane is very unstable in both soil and water, and in the environment it exists as abiotic transformation products, tricyclo[2.2.1.02,6]heptan-3-ol and bicyclo[2.2.1]hept-5-en-2-ol. In soils, tricyclo[2.2.1.02,6]heptan-3-ol is microbially transformed to a C7H8O intermediate which we postulate to be tricyclo[2.2.1.02,6]heptan-3-one. This co

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23

Yates, Peter, D. Jean Burnell, Vernon J. Freer, and Jeffery F. Sawyer. "Synthesis of cedranoid sesquiterpenes. III. Functionalization at carbon 4." Canadian Journal of Chemistry 65, no. 1 (1987): 69–77. http://dx.doi.org/10.1139/v87-012.

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Dimethyl 6,6-dimethyl-5,7-dioxobicyclo[2.2.2]oct-2-ene-2,3-dicarboxylate (8) on irradiation in acetophenone gives dimethyl 6,6-dimethyl-4,7-dioxotricyclo[3.2.1.02,8]octane-1,8-dicarboxylate (13), which on treatment with lithium dimethylcuprate followed by monodecarbomethoxylation gives methyl 4,4-endo-8-trimethyl-3,6-dioxo-cis-bicyclo[3.3.0]octane-1-carboxylate (17). Similar irradiation of dimethyl 4,6,6-trimethyl-5,7-dioxobicyclo[2.2.2]oct-2-ene-2,3-dicarboxylate (24) and its 7,7-ethylenedioxy derivative (25) followed by treatment with DBU and concentrated H2SO4, respectively, gives dimethyl

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24

Cha, Jin, Sejin Lee, and Keunho Kim. "A Semi-Pinacol Rearrangement Approach to Bicyclo[3.2.1]octan-2-ones and Bicyclo[3.2.1]octan-3-ones." Synlett 2008, no. 14 (2008): 2155–57. http://dx.doi.org/10.1055/s-2008-1077902.

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25

Trost, Barry M., Patrick J. McDougall, Olaf Hartmann, and Peter T. Wathen. "Asymmetric Synthesis of Bicyclo[4.3.1]decadienes and Bicyclo[3.3.2]decadienes via [6 + 3] Trimethylenemethane Cycloaddition with Tropones." Journal of the American Chemical Society 130, no. 45 (2008): 14960–61. http://dx.doi.org/10.1021/ja806979b.

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26

Li, Qing, Dang Quan Zhang, Qi Mei Liu та Kuan Peng. "Determination of Bioactive Components of 60°С Volatiles from Cinnamomum camphora Branches by TD-GC/MS". Advanced Materials Research 230-232 (травень 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

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27

Hertkorn, N., and F. H. Köhler. "Selektive Metallierung von BicycIo[3.2.1]octa-2,6-dien, II Distannylierte Derivate und stannylierte tricyclische Sekundärprodukte / Selective Metalation of Bicyclo[3.2.1]octa-2,6-diene, II Distannylated Derivatives and Stannylated Tricyclic Secondary Products." Zeitschrift für Naturforschung B 43, no. 11 (1988): 1405–15. http://dx.doi.org/10.1515/znb-1988-1105.

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Abstract Distannylated bicyclo[3.2.1]octa-2,6-diene (1) with (CH3)3 Sn groups in positions exo-4 and 7 (7a), endo-4 and 7 (7b), exo-4 and 6 (7c), and probably exo-4 and endo-4 (7d) are obtained when 1 is treated first with an excess of n-BuLi/t-BuOK in alkane and then with (CH3)3 SnCl. Byproducts are monostannylated derivatives of 1 and l,4-bis(trimethylstannyl)but-2-ene (3). The formation of 7a/b/c is best understood when the two possible bicyclo[3.2.1]octa-2,6-dienyl dianions are generated as intermediates. 3,exo-4-Bis(trimethylstannyl)bicyclo[3.2.1]octa-2,6-diene (7e) is ob-tained from the

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28

Stritt, H. P., H. J. Wörz, and H. P. Latscha. "Bildungsmechanismus und Folgereaktionen von 1.2.5.6-Tetraphospha-3.4—7.8-dibenzo-2.6-diiodo-bicycIo[3.3.0]octan Elektrochemische Darstellung von 1.2.5.6-Tetraphospha-3.4—7.8-dibenzo-2.6-dichloro-bicyclo[3.3.0]octan / Formation and Reaction Products of 1.2.5.6-Tetraphospha-3.4—7.8-dibenzo-2.6-diiodo-bicyclo[3.3.0]octane Electrochemical Synthesis of 1.2.5.6-Tetraphospha-3.4—7.8-dibenzo-2.6-diiodo-bicyclo[3.3.0]octane." Zeitschrift für Naturforschung B 40, no. 12 (1985): 1711–14. http://dx.doi.org/10.1515/znb-1985-1218.

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Abstract The reaction of o-phenylene-bis(dichlorophosphane) (1) [2] with anhydrous Lil in benzene gives o-phenylene-bis(diiodophosphane) (2). In the presence of water the reaction leads to the bicyclus 3 [1], Electrolysis of 1 with a mercury-pool at a potential of -800 mV in a 1.2-dichloroethane/ 0.1 Mtetrabutylammonium tetrafluoroborate solution gives 1.2.5.6-tetraphospha- 3.4-7.8-dibenzo-2.6-dichloro-bicyclo[3.3.0]octane (4). The reduction of 3, either by magnesium in THF or by electrolysis in 1.2-DCE/0.1 M TBATFB solution at a potential of -1 V yields the oligomer (o-C6H4P2)5

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29

Liu, Qi Mei, Dang Quan Zhang, Kuan Peng та Wan Xi Peng. "Deep Analysis on Bioindustry Prospects of 40°С Volatiles of Cinnamomum camphora Branches". Key Engineering Materials 480-481 (червень 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)

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30

Pigou, PE, and DK Taylor. "Activation Parameters for Ring Opening of (Bicyclo[n.1.1]alk-1-yl)methyl Radicals." Australian Journal of Chemistry 44, no. 10 (1991): 1417. http://dx.doi.org/10.1071/ch9911417.

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Ring opening of the (bicyclo[1.1.1]pent-1-yl)methyl (4), (bicyclo[2.1.1]hex-1-yl)methyl (5) and (bicyclo[3.1.1]hept-1-yl)methyl (6) radicals has been investigated by semiempirical molecular orbital theory MINDO/3 and AM1) and by experiment. Our results indicate that (4) ring-opens extremely rapidly, with an estimated energy barrier of less than 22 kJ mol-1. The higher homologues (5) and (6) rearrange more slowly with barriers of about 42.2 and 46.0 kJ mol-1 respectively. This trend is also observed in the MINDO/3 and AM1 results, with the latter giving the better agreement with experiment.

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31

Werstiuk, Nick Henry, та 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, № 3 (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

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32

Šála, Michal, Hubert Hřebabecký, Martin Dračínský, et al. "Synthesis of novel racemic carbocyclic nucleosides derived from 5,6-disubstituted norbornene." Collection of Czechoslovak Chemical Communications 75, no. 1 (2009): 1–20. http://dx.doi.org/10.1135/cccc2009116.

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Novel class of the carbocyclic nucleosides based on bicyclo[2.2.1]heptene/heptane was prepared by two approaches. Thymine analogues were synthesized starting from methyl (1R*,4S*)-bicyclo[2.2.1]hepta-2,5-diene-2-carboxylate1by Michael addition of the thymine salt to the double bond as the key step. The yield and ratio of the isomers of this reaction depended on the used base (DBU, K2CO3). Purine nucleoside analogues were synthesized by the linear synthesis, the purine nucleobase was build-up on the amino group. The amino groups (exo/endoconfiguration) were introduced to the scaffold by the Cur

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33

Thirumoorthi, Navanita T., and Vikrant A. Adsool. "A practical metal-free homolytic aromatic alkylation protocol for the synthesis of 3-(pyrazin-2-yl)bicyclo[1.1.1]pentane-1-carboxylic acid." Organic & Biomolecular Chemistry 14, no. 40 (2016): 9485–89. http://dx.doi.org/10.1039/c6ob01799a.

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As a part of our ongoing synthetic quest to expand the frontiers of contemporary medicinal chemistry, we now report an expedient synthesis of a potentially useful bicyclo[1.1.1]pentane building block, 3-(pyrazin-2-yl)bicyclo[1.1.1]pentane-1-carboxylic acid. This report also showcases the application of this motif as a “spacer” probe in a biological study.

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34

Ngamga, Dieudonne, Josephine Bipa, Pearl Lebatha, et al. "Isoquinoline Alkaloids and Homoisoflavonoids from Drimiopsis barteri Bak and D. burkei Bak." Natural Product Communications 3, no. 5 (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-isofla

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Russell Bowman, W., David S. Brown, Catherine A. Burns, Brian A. Marples, and Naveed A. Zaidi. "Radical reactions of bicyclo[2.2.1]heptan-3-spiro-2′-oxiranes." Tetrahedron 48, no. 33 (1992): 6883–96. http://dx.doi.org/10.1016/s0040-4020(01)89879-3.

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Hambalek, Robeart, and George Just. "Trisubstituted oxetanes from 2,7-dioxa-bicyclo-[3,2,0]-hept-3-enes." Tetrahedron Letters 31, no. 33 (1990): 4693–96. http://dx.doi.org/10.1016/s0040-4039(00)97708-6.

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37

Buchbauer, Gerhard, Johanna Gabmeier, Ernst Haslinger, Wolfgang Robien, and Harald Steindl. "Synthese und Reaktionen von Bicyclo[6.4.0]dodecan-3-carbonsäure-Derivaten." Helvetica Chimica Acta 68, no. 1 (1985): 231–35. http://dx.doi.org/10.1002/hlca.19850680129.

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Luger, Peter, Manuela Weber, Günter Szeimies, and Michael Pätzel. "3-(tert-Butyloxycarbonylamino)bicyclo[1.1.1]pentanecarboxylic acid at 293 K." Acta Crystallographica Section C Crystal Structure Communications 56, no. 9 (2000): 1170–72. http://dx.doi.org/10.1107/s0108270100008994.

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39

Liao, Zhehui, Jiantao Zhang, Tongxiang Cao, and Shifa Zhu. "Copper-Catalyzed Asymmetric Synthesis of Bicyclo[3.n.1]alkenones." Journal of Organic Chemistry 86, no. 7 (2021): 5388–400. http://dx.doi.org/10.1021/acs.joc.1c00146.

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40

Zhu, Fang-Hua, Jun-Xiao Yang, Lin Zhang, and Ru-Gang Xie. "1-[Bicyclo[4.2.0]octa-1(6),2,4-trien-3-yl]-3-(but-3-enyl)imidazolium bromide." Acta Crystallographica Section E Structure Reports Online 64, no. 2 (2008): o433. http://dx.doi.org/10.1107/s1600536807058114.

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Yu, Zhi-Xiang, and Cheng-Hang Liu. "Rh(I)-Catalyzed Intramolecular [3+2] Cycloaddition of trans-2-Allene-Vinylcyclopropanes." Synlett 29, no. 06 (2018): 764–68. http://dx.doi.org/10.1055/s-0037-1609199.

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42

Ji, Jianguo, William H. Bunnelle, Tao Li та ін. "Discovery of fused azetidines as novel selective α4β2 neuronal nicotinic receptor (NNR) agonists". Pure and Applied Chemistry 77, № 12 (2005): 2041–45. http://dx.doi.org/10.1351/pac200577122041.

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An efficient synthesis of (1R,5S)-6-(5-cyano-3-pyridinyl)-3,6-diaza-bicyclo[3.2.0]heptane A-366833, a novel potent selective neuronal nicotinic receptor (NNR) agonist, is described. The enantiomerically pure pharmacophore benzyl (1S,5S)-3,6-diaza-bicyclo[3.2.0]heptane-3-carbamate was successfully constructed from benzyl N-allyl-N-(2-hydroxyimino-ethyl)-carbamate through a convenient approach including an intramolecular [1,3]-dipolar cycloaddition, reductive ring-opening reaction, chiral resolution, and intramolecular cyclization. Subsequent N-arylation of the pharmacophore with 3-bromo-5-cyano

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43

Mackay, M. F., G. P. Savage, and G. W. Simpson. "3'-(2,6-Dichlorophenyl)bicyclo[2.2.1]heptane-2-spiro-5'(4'H)-isoxazole-3-one." Acta Crystallographica Section C Crystal Structure Communications 50, no. 11 (1994): 1772–74. http://dx.doi.org/10.1107/s0108270194004622.

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44

Hooft, R. W. W., and J. Kroon. "3'-Methoxyspiro[bicyclo[3.1.0]hexane-6,16'-estra-1',3',5'(10')-trien]-17'-one." Acta Crystallographica Section C Crystal Structure Communications 51, no. 4 (1995): 721–23. http://dx.doi.org/10.1107/s0108270194008899.

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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 (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

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46

Pathipati, Stalin R., Lars Eriksson, and Nicklas Selander. "Stereoselective synthesis of bicyclo[3.n.1]alkenone frameworks by Lewis acid-catalysis." Chem. Commun. 53, no. 82 (2017): 11353–56. http://dx.doi.org/10.1039/c7cc06400d.

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47

Muriel, Bastian, Alec Gagnebin, and Jerome Waser. "Synthesis of bicyclo[3.1.0]hexanes by (3 + 2) annulation of cyclopropenes with aminocyclopropanes." Chemical Science 10, no. 46 (2019): 10716–22. http://dx.doi.org/10.1039/c9sc03790j.

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BEDEKAR, A. V., H. A. PATEL, K. B. NAIR, and R. SOMAN. "ChemInform Abstract: Facile Syntheses of cis-Bicyclo(3.3.0)oct-3-ene-2,6-dione and cis- Bicyclo(3.3.0)oct-3-en-2-on-6-yl Acetate." ChemInform 25, no. 44 (2010): no. http://dx.doi.org/10.1002/chin.199444095.

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49

Marotta, Emanuela, Ilaria Pagani, Paolo Righi, Goffredo Rosini, Valerio Bertolasi, and Alessandro Medici. "Pure enantiomers of bicyclo[3.2.0]hept-3-en-6-ones and bicyclo[3.2.0]hept-3-en-6-endo-ols: Resolution, absolute configuration and optical properties." Tetrahedron: Asymmetry 6, no. 9 (1995): 2319–28. http://dx.doi.org/10.1016/0957-4166(95)00308-c.

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50

Collis, Gavin E., Dylan Jayatilaka, and Dieter Wege. "Cyclopropa-Fused Quinones. The Generation and Trapping of Bicyclo[4.1.0]hepta-1(6),3-diene-2,5-dione and 1H-Cyclopropa[b]naphthalene-2,7-dione." Australian Journal of Chemistry 50, no. 5 (1997): 505. http://dx.doi.org/10.1071/c96204.

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The title compounds (3) and (4) have been generated at low temperature by debromosilylation of 1-bromo-6-trimethylsilylbicyclo[4.1.0]hept-3-ene-2,5-dione (23) and 1a-bromo-7a-trimethylsilyl-1a,7a-dihydro-1H-cyclopropa[b]naphthalene-2,7-dione (38) respectively. Both cyclopropa-fused quinones are reactive but each could be trapped with furan to give a pair of cycloadducts, which were remarkably resistant to cycloreversion. In the absence of added trapping agent, the cyclopropanaphthoquinone (4) was intercepted by fluoride ion to give 1a-fluoro-1a,7a-dihydro-1H-cyclopropa[b]naphthalene-2,7-dione

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