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Journal articles on the topic 'Bicyclo[2'

Author: Grafiati

Published: 4 June 2021

Last updated: 18 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 (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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2

Tabuchi, Toshiki, Daisuke Urabe, and Masayuki Inoue. "Asymmetric synthesis of a highly functionalized bicyclo[3.2.2]nonene derivative." Beilstein Journal of Organic Chemistry 9 (April 4, 2013): 655–63. http://dx.doi.org/10.3762/bjoc.9.74.

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The stereoselective Diels–Alder reaction between an optically active 1,4-dimethylcycloheptadiene and acrolein was effectively promoted by TBSOTf to produce a bicyclo[3.2.2]nonene derivative bearing two quaternary carbons. Seven additional transformations from the obtained bicycle delivered the C 2-symmetric bicyclo[3.3.2]decene derivative, a key intermediate in our synthetic study of ryanodine.

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3

Smith, William B. "Nature of the 2-Bicyclo[3.2.1]octanyl and 2-Bicyclo[3.2.2]nonanyl Cations." Journal of Organic Chemistry 66, no. 2 (January 2001): 376–80. http://dx.doi.org/10.1021/jo0006167.

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4

Piers, Edward, and Hoi Lun Allan Tse. "A new annulation method. Total syntheses of the sesquiterpenoids (±)-chiloscyphone and (±)-6-epi-chiloscyphone." Canadian Journal of Chemistry 71, no. 7 (July 1, 1993): 983–94. http://dx.doi.org/10.1139/v93-131.

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The efficacy of a new annulation method, developed for the construction of functionalized bicyclic compounds, is illustrated by conversion of the β-keto esters 18 and 19 into the bicyclo[4.3.0]non-1-enes 33 and 34, respectively, and by transformation of 2-methoxycarbonylcyclopentanone (20) into the bicyclo[4.3.0]non-6-ene 38 and the bicyclo[5.3.0]dec-7-enes 48 and 51. Application of the method to total syntheses of the structurally unusual sesquiterpenoids (±)-chiloscyphone (16) and (±)-6-epi-chiloscyphone (17) is described.

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5

Wiberg, Kenneth B., Brenda S. Ross, John J. Isbell, and Neil McMurdie. "2-Substituted bicyclo[1.1.1]pentanes." Journal of Organic Chemistry 58, no. 6 (March 1993): 1372–76. http://dx.doi.org/10.1021/jo00058a015.

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6

Carrupt, Pierre-Alain, and Pierre Vogel. "Double bond pyramidalization in bicyclic alkanes. Ab initio mo calculations on bicyclo[2.2.1] hept-2-ene, bicyclo[2.2.1] hex-2-ene and bicyclo[3.2.1] oct-6-ene derivatives." Journal of Molecular Structure: THEOCHEM 124, no. 1-2 (January 1985): 9–23. http://dx.doi.org/10.1016/0166-1280(85)87017-2.

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7

Gilbert, John C., and Jiandong Yin. "Interconversion of Bicyclo[2.2.1]hept-2-yne and 5-Bicyclo[2.1.1]hexylidenecarbene." Journal of Organic Chemistry 71, no. 15 (July 2006): 5658–61. http://dx.doi.org/10.1021/jo060652r.

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8

Eberle, Marcel K., Reinhart Keese, and Helen Stoeckli-Evans. "A bicyclo[3.3.0]octan-2-ylcyclopentanone." Acta Crystallographica Section E Structure Reports Online 57, no. 5 (April 30, 2001): o461—o462. http://dx.doi.org/10.1107/s1600536801006808.

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9

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)amino]-5-(hydroxymethyl)- bicyclo[2.2.1]hept-5-en-2-ol (17a) and (1R*,2R*,3S*,4S*)-3-[(5-amino-6-chloropyrimidin-4-yl)- amino]-6-(hydroxymethyl)bicyclo[2.2.1]hept-5-en-2-ol (17b). Ring closure with triethyl orthoformate led to (1R*,2R*,3S*,4S*)-5-(chloromethyl)-3-(6-chloro-9H-purin-9-yl)bicyclo[2.2.1]hept-5-en-2-ol (18a) and (1R*,2R*,3S*,4S*)-6-(chloromethyl)-3-(6-chloro-9H-purin-9-yl)- bicyclo[2.2.1]hept-5-en-2-ol (18b) using hydrochloric acid as a catalyst or (1R*,2R*,3S*,4S*)-3-(6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)bicyclo[2.2.1]hept-5-en-2-ol (19a) and (1R*,2R*,3S*,4S*)- 3-(6-chloro-9H-purin-9-yl)-6-(hydroxymethyl)bicyclo[2.2.1]hept-5-en-2-ol (19b) using trifluoro- acetic acid as a catalyst. From19aand19b, 6-amino- and 6-(cyclopropylamino)purine derivatives20and21were prepared.

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10

Ishibashi, Osamu, Mami Nishiyama, Eunsang Kwon, Masaru Hashimoto, Shigefumi Kuwahara, and Masaru Enomoto. "Semipinacol rearrangement of a bicyclo[7.2.0]undecane framework into a bicyclo[6.3.0]undecane skeleton: a model study on the biosynthesis of seiridiasteriscane A." Bioscience, Biotechnology, and Biochemistry 85, no. 7 (May 7, 2021): 1621–27. http://dx.doi.org/10.1093/bbb/zbab083.

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ABSTRACT Seiridiasteriscane A is an asteriscane-type sesquiterpenoid bearing a trans-fused bicyclo[6.3.0]undecane skeleton. Although its biosynthesis has been proposed to involve a semipinacol rearrangement of a putative intermediary acetate bearing a bicyclo[7.2.0]undecane ring system (presumably derived from coisolated pestalotiopsin M) followed by epimerization of the resulting cis-fused seiridiasteriscane B, such a type of semipinacol rearrangement has never been reported so far. Our model study revealed that a 1-hydroxybicyclo[7.2.0]undecan-2-yl acetate underwent a smooth and stereospecific semipinacol rearrangement with the assistance of Et2AlCl to give the corresponding bicyclo[6.3.0]undecane-9-one. In addition, the resulting cis-fused 5,8-bicyclic ketone was partially epimerized to the corresponding trans-fused ketone by prolonged adsorption onto a silica gel plate. These results may support a recently proposed biosynthetic pathway of seiridiasteriscane A.

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11

Baldwin, John E., and Kevin D. Belfield. "Stereochemistry of the thermal isomerization of bicyclo[3.2.0]hept-2-ene to bicyclo[2.2.1]hept-2-ene." Journal of the American Chemical Society 110, no. 1 (January 1988): 296–97. http://dx.doi.org/10.1021/ja00209a051.

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12

Seebacher, Werner, Christian Schlapper, Reto Brun, Marcel Kaiser, Robert Saf, and Robert Weis. "Antiprotozoal activities of new bicyclo[2.2.2]octan-2-imines and esters of bicyclo[2.2.2]octan-2-ols." European Journal of Pharmaceutical Sciences 24, no. 4 (March 2005): 281–89. http://dx.doi.org/10.1016/j.ejps.2004.11.003.

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13

KUMADA, Kouji. "5-Ethylidene bicyclo [2.2.1] hept-2-ene." Journal of Synthetic Organic Chemistry, Japan 47, no. 3 (1989): 265–66. http://dx.doi.org/10.5059/yukigoseikyokaishi.47.265.

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14

Allal, Badia Ait, Larbi El Firdoussi, Smail Allaoud, and Abdellah Karim. "4,7,7-Trimethyl-bicyclo [2.2.1]heptan-2-ol." Molecules 6, no. 12 (May 25, 2001): M239. http://dx.doi.org/10.3390/m239.

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15

WIBERG, K. B., B. S. ROSS, J. J. ISBELL, and N. MCMURDIE. "ChemInform Abstract: 2-Substituted Bicyclo(1.1.1)pentanes." ChemInform 24, no. 27 (August 20, 2010): no. http://dx.doi.org/10.1002/chin.199327161.

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16

Hartmann, M. "Einfache Synthese des Bicyclo[3,3,1]nonanon-(2)." Zeitschrift für Chemie 6, no. 5 (September 2, 2010): 182. http://dx.doi.org/10.1002/zfch.19660060505.

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17

Bentley, T. William, Bernd Engels, Thomas Hupp, Elena Bogdan, and Manfred Christl. "Unsubstituted Bicyclo[1.1.0]but-2-ylcarbinyl Cations." Journal of Organic Chemistry 71, no. 3 (February 2006): 1018–26. http://dx.doi.org/10.1021/jo0519918.

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18

Mukai, Chisato, Yasuyuki Hara, Yusuke Miyashita, and Fuyuhiko Inagaki. "Thermal [2+2] Cycloaddition of Allenynes: Easy Construction of Bicyclo[6.2.0]deca-1,8-dienes, Bicyclo[5.2.0]nona-1,7-dienes, and Bicyclo[4.2.0]octa-1,6-dienes." Journal of Organic Chemistry 72, no. 12 (June 2007): 4454–61. http://dx.doi.org/10.1021/jo070513p.

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19

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*)-3-(6-chloro-9H-purin-9-yl)-6,6-bis(hydroxymethyl)bicyclo[2.2.1]heptan-2-ol (21b), and (1R*,2S*,3S*,4S*)-3-(6-chloro-9H-purin-9-yl)-5,5-bis(hydroxymethyl)bicyclo[2.2.1]heptan-2-ol (21c), respectively. Ammonolysis of these compounds led to 6-amino-9H-purine derivatives22a-22c. 6-(Dimethylamino)-9H-purine analogues23a-23cand 6-(cyclopropylamino)-9H-purine analogues24a-24cwere prepared by aminolysis of21a-21c. Reaction of amines13,18, and19with ethylN-((2E)-3-ethoxymethacryloyl)carbamate afforded thymine derivatives28a-28c.

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20

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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21

Kirmse, Wolfgang, and Bernhard Goer. "1-Cyano- and 2-cyano-2-bicyclo[2.1.1]hexyl cations." Journal of the American Chemical Society 112, no. 11 (May 1990): 4556–57. http://dx.doi.org/10.1021/ja00167a070.

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22

Kiattansakul, Rattana, and John K. Snyder. "Cobalt-catalyzed [4 + 2 + 2] cycloadditions of bicyclo[2.2.2]octadienes." Tetrahedron Letters 40, no. 6 (February 1999): 1079–82. http://dx.doi.org/10.1016/s0040-4039(98)02632-x.

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23

Gasanov, A. G., and A. V. Nagiev. "Synthesis of 2-(Bicyclo[2.2.1]hept-2-yloxy)ethyl Carboxylates." Russian Journal of Organic Chemistry 41, no. 12 (December 2005): 1755–56. http://dx.doi.org/10.1007/s11178-006-0033-9.

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24

Katayama, Sadamu, Hajime Hiramatsu, Keiichi Aoe, and Masashige Yamauchi. "Synthesis of bicyclo[4.1.0]hept-2-enes (trinorcarenes) by photochemical reaction of bicyclo[2.2.2]oct-5-en-2-ones." Journal of the Chemical Society, Perkin Transactions 1, no. 4 (1997): 561–76. http://dx.doi.org/10.1039/a601900e.

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25

Chen, Yan, and John K. Snyder. "Opening the [4 + 2 + 2] Cycloadducts of Bicyclo[2.2.1]hepta-2,5-dienes (Norbornadienes) to Cis-Fused Bicyclo[5.3.0]decanes1." Journal of Organic Chemistry 66, no. 21 (October 2001): 6943–57. http://dx.doi.org/10.1021/jo010269g.

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26

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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27

Behrendt, Uwe, Barbara Gabor, Richard Mynott, and Holger Butenschön. "Rearrangement of a Bicyclo[3.2.0]hept-2-ene to a Bicyclo[4.1.0]hept-4-ene." Liebigs Annalen 1996, no. 7 (January 25, 2006): 1167–73. http://dx.doi.org/10.1002/jlac.199619960716.

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28

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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29

Kirmse, Wolfgang, Volker Zellmer, and Bernhard Goer. "Nucleophilic capture of 2-bicyclo[2.1.1]hexyl cations." Journal of the American Chemical Society 108, no. 16 (August 1986): 4912–17. http://dx.doi.org/10.1021/ja00276a035.

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30

Kirmse, Wolfgang, and Joachim Streu. "2-Bicyclo[3.2.0]heptyl and 7-norbornyl cations." Journal of Organic Chemistry 50, no. 22 (November 1985): 4187–94. http://dx.doi.org/10.1021/jo00222a003.

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31

Powers, David C., Phyllis A. Leber, Sarah S. Gallagher, Andrew T. Higgs, Lynne A. McCullough, and John E. Baldwin. "Thermal Chemistry of Bicyclo[4.2.0]oct-2-enes." Journal of Organic Chemistry 72, no. 1 (January 2007): 187–94. http://dx.doi.org/10.1021/jo061964x.

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32

Katayama, Sadamu, and Masashige Yamauchi. "Photochemical Synthesis of Bicyclo[4.1.0]hept-2-enes." Chemistry Letters 24, no. 4 (April 1995): 311–12. http://dx.doi.org/10.1246/cl.1995.311.

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33

Malinowska, Anna, Izabela Czeluśniak, Marcin Górski, and Teresa Szymańska-Buzar. "A novel catalytic route to 2-bicyclo[2.2.1]hept-2-ylidenebicyclo[2.2.1]-heptane involving CH bond activation of bicyclo[2.2.1]hept-2-ene." Journal of Molecular Catalysis A: Chemical 226, no. 2 (February 2005): 259–62. http://dx.doi.org/10.1016/j.molcata.2004.10.040.

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34

Cotterill, Ian C., Emma L. A. Macfarlane, and Stanley M. Roberts. "Resolution of bicyclo[3.2.0]hept-2-en-6-ols and bicyclo[4.2.0]oct-2-en-endo-7-ol using lipases." Journal of the Chemical Society, Perkin Transactions 1, no. 12 (1988): 3387. http://dx.doi.org/10.1039/p19880003387.

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35

Inagaki, Fuyuhiko, Syu Narita, Takuma Hasegawa, Shinji Kitagaki, and Chisato Mukai. "Rhodium(I)-Catalyzed Intramolecular Carbonylative [2+2+1] Cycloaddition of Bis(allene)s: Bicyclo[6.3.0]undecadienones and Bicyclo[5.3.0]decadienones." Angewandte Chemie International Edition 48, no. 11 (March 2, 2009): 2007–11. http://dx.doi.org/10.1002/anie.200806029.

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36

Inagaki, Fuyuhiko, Syu Narita, Takuma Hasegawa, Shinji Kitagaki, and Chisato Mukai. "Rhodium(I)-Catalyzed Intramolecular Carbonylative [2+2+1] Cycloaddition of Bis(allene)s: Bicyclo[6.3.0]undecadienones and Bicyclo[5.3.0]decadienones." Angewandte Chemie 121, no. 11 (March 2, 2009): 2041–45. http://dx.doi.org/10.1002/ange.200806029.

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37

Chen, Yan, Rattana Kiattansakul, Bin Ma, and John K. Snyder. "Transition Metal-Catalyzed [4 + 2 + 2] Cycloadditions of Bicyclo[2.2.1]hepta-2,5-dienes (Norbornadienes) and Bicyclo[2.2.2]octa-2,5-dienes1." Journal of Organic Chemistry 66, no. 21 (October 2001): 6932–42. http://dx.doi.org/10.1021/jo010268o.

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38

Davenel, Vincent, Chloé Puteaux, Christian Nisole, Fabien Fontaine-Vive, Jean-Marie Fourquez, and Véronique Michelet. "Indium-Catalyzed Cycloisomerization of 1,6-Cyclohexenylalkynes." Catalysts 11, no. 5 (April 24, 2021): 546. http://dx.doi.org/10.3390/catal11050546.

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Efficient four- and five-step routes to access functionalized bicyclo[3.2.1]oct-2-ene and bicyclo[3.3.1]nonadiene via indium-mediated cycloisomerization of 1,6-enynes has been developed. This atom-economical catalytic process was optimized and relied on the efficiency of InCl3 leading to the preparation of functionalized bicyclic adducts in up to 99% isolated yield. The cyclization occurred on two different processes (5-exo versus 6-endo pathway) and were influenced by the substitution of the alkynyl moiety. The exo process was favored for non-substituted alkynes whereas the endo pathway was generally observed for substituted alkynes. Then, the presence of electron-withdrawing groups on the aryl substituted alkyne increased the ratio of the exo isomer. DFT calculations were performed on stability of intermediates and corroborated the intervention of InCl3.

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39

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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40

Levchenko, Konstantin S., Konstantin A. Chudov, Dmitri Yu Demin, Konstantin A. Lyssenko, and Pavel S. Shmelin. "2-(Bicyclo[4.2.0]octa-1,3,5-trien-3-yl)-adamantan-2-ol." Molbank 2020, no. 1 (January 10, 2020): M1106. http://dx.doi.org/10.3390/m1106.

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A new adamantan-2-ol with a 2-bicyclo[4.2.0]octa-1,3,5-trien-3-yl substituent in the position 2 was synthesized via two stage synthesis starting from benzocyclobutene and adamatan-2-one. The structure of the title compound was determined using 1H-and 13C-NMR, HRMS and XRD.

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41

Yu, Zhi-Xiang, and Cheng-Hang Liu. "Rh(I)-Catalyzed Intramolecular [3+2] Cycloaddition of trans-2-Allene-Vinylcyclopropanes." Synlett 29, no. 06 (January 18, 2018): 764–68. http://dx.doi.org/10.1055/s-0037-1609199.

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42

Bentley, T. William, Simon J. Norman, Ralf Kemmer, and Manfred Christl. "Synthesis and Solvolysis of Bicyclo[3.1.1]hept-3-en-2-yl, Bicyclo[3.1.1]hept-2-yl, and 2-Halogenocyclohex-2-en-1-yl Methanesulfonates andp-Nitrobenzoates." Liebigs Annalen 1995, no. 4 (April 1995): 599–608. http://dx.doi.org/10.1002/jlac.199519950483.

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43

Knotnerus, J., and H. Schilling. "Bicyclanes: V. New syntheses of cis-bicyclo[3.3.0]octane and cis-bicyclo[3.3.0]oct-2-ene." Recueil des Travaux Chimiques des Pays-Bas 83, no. 11 (September 2, 2010): 1185–90. http://dx.doi.org/10.1002/recl.19640831110.

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44

Jasiński, Radomir, Oskar Koifman, and Andrzej Barański. "A B3LYP/6-31G(d) study of Diels-Alder reactions between cyclopentadiene and (E)-2-arylnitroethenes." Open Chemistry 9, no. 6 (December 1, 2011): 1008–18. http://dx.doi.org/10.2478/s11532-011-0088-5.

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AbstractThe B3LYP/6-31G(d) simulations of competing CDA and HDA reactions between cyclopentadiene and (E)-2-arylnitroethenes prove that regardless of the medium polarity, the processes leading to respective 5-nitro-6-aryl-bicyclo-[2,2,0]-hept-2-enes 3,4 (paths A and B) should be most favoured, and the more electrophilic (E)-2-(p-nitrophenyl)-nitroethene should be more reactive than the less electrophilic (E)-2-(p-methoxyphenyl)-nitroethene. Asymmetry of the transition complexes on the favoured pathways increases with increase of medium polarity, but not sufficiently to enforce the zwitterionic mechanism. Analysis of competing pathways leading to HDA adducts proves that not all these compounds can be formed directly from the adducts. In particular, on the path C, the initially formed 5-nitro-6-aryl-bicyclo-[2,2,0]-hept-2-enes 3 is converted to 2-phenyl-4-aza-5-oxy-bicyclo-[3,4,0]-nona-3,7-diene N-oxides 5 as a result of a [3.3]-sigmatropic shift. On the paths D–F leading to 2-phenyl-4-aza-5-oxy-bicyclo-[3,4,0]-nonadienes N-oxides 6–8, the reaction proceeds according to a one-step mechanism.

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45

Watson, W. H., and R. P. Kashyap. "Bicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylic anhydride (1), C9H6O3, and bicyclo[2.2.1]hept-2-ene-2,3-dicarboxylic anhydride (2), C9H8O3." Acta Crystallographica Section C Crystal Structure Communications 41, no. 8 (August 15, 1985): 1226–29. http://dx.doi.org/10.1107/s0108270185007223.

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46

Willetts, Andrew J., Christopher J. Knowles, Melissa S. Levitt, Stanley M. Roberts, Helen Sandey, and Nigel F. Shipston. "Biotransformation of endo-bicyclo[2.2.1 ]heptan-2-ols and endo-bicyclo[3.2.0]hept-2-en-6-ol into the corresponding lactones." Journal of the Chemical Society, Perkin Transactions 1, no. 6 (1991): 1608. http://dx.doi.org/10.1039/p19910001608.

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47

KATAYAMA, S., H. HIRAMATSU, K. AOE, and M. YAMAUCHI. "ChemInform Abstract: Synthesis of Bicyclo(4.1.0)hept-2-enes (Trinorcarenes) by Photochemical Reaction of Bicyclo(2.2.2)oct-5-en-2-ones." ChemInform 28, no. 29 (August 3, 2010): no. http://dx.doi.org/10.1002/chin.199729071.

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48

Chen, Yan, and John K. Snyder. "ChemInform Abstract: Opening the [4 + 2 + 2] Cycloadducts of Bicyclo[2.2.1]hepta-2,5-dienes (Norbornadienes) to cis-Fused Bicyclo[5.3.0]decanes." ChemInform 33, no. 12 (May 22, 2010): no. http://dx.doi.org/10.1002/chin.200212065.

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49

Thirunarayanan, Ganesamoorthy. "Bio-Potent (5-Chloro-2-Thienyl)-3-(Substituted Phenyl) Bicyclo[2.2.1]Heptane-2-yl Methanone Derivatives." International Letters of Chemistry, Physics and Astronomy 42 (December 2014): 1–12. http://dx.doi.org/10.18052/www.scipress.com/ilcpa.42.1.

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A series of (5-chloro-2-thienyl)(3-(substituted phenyl) bicyclo [2.2.1] hept-5-en-2-yl) methanones have been synthesized by fly-ash catalyzed [4+2] cycloaddition Diels-Alder reaction of cyclopentadiene and 5-chloro-2-thienyl chalcones under cooling conditions. The yields of the methanones are more than 60%. The synthesized (5-chloro-2-thienyl)(3-(substituted phenyl) bicyclo [2.2.1] hept-5-en-2-yl) methanones are characterized by their physical constants and spectral data. The antimicrobial, antioxidant and insect antifeedant activities of synthesized methanones have been studied using their respective bacterial, fungal strains, DPPH radical scavenging activity and Dethler’s leaf-discs bioassay method.

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50

Pradal, Alexandre, Chung-Meng Chao, Patrick Y. Toullec, and Véronique Michelet. "Asymmetric Au-catalyzed cycloisomerization of 1,6-enynes: An entry to bicyclo[4.1.0]heptene." Beilstein Journal of Organic Chemistry 7 (July 26, 2011): 1021–29. http://dx.doi.org/10.3762/bjoc.7.116.

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A comprehensive study on the asymmetric gold-catalyzed cycloisomerization reaction of heteroatom tethered 1,6-enynes is described. The cycloisomerization reactions were conducted in the presence of the chiral cationic Au(I) catalyst consisting of (R)-4-MeO-3,5-(t-Bu)2-MeOBIPHEP-(AuCl)2 complex and silver salts (AgOTf or AgNTf2) in toluene under mild conditions to afford functionalized bicyclo[4.1.0]heptene derivatives. The reaction conditions were found to be highly substrate-dependent, the best results being obtained in the case of oxygen-tethered enynes. The formation of bicyclic derivatives, including cyclopropyl pentasubstituted ones, was reported in moderate to good yields and in enantiomeric excesses up to 99%.

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