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Journal articles on the topic 'Bicyclo[4'

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Published: 4 June 2025

Last updated: 1 August 2025

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1

Corfield, Peter W. R., and Richard A. Kershaw. "Crystal structures of two bicyclo[5.1.0]octanes: potassiumtrans-bicyclo[5.1.0]octane-4-carboxylate monohydrate andcis-bicyclo[5.1.0]octan-4-yl 4-bromobenzenesulfonate." Acta Crystallographica Section E Crystallographic Communications 73, no. 9 (2017): 1357–62. http://dx.doi.org/10.1107/s2056989017011756.

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The crystal structures of thetrans-fused compound potassiumtrans-bicyclo[5.1.0]octane-4-carboxylate monohydrate, K+·C9H13O2−·H2O, (I), and ofcis-bicyclo[5.1.0]octan-4-yl 4-bromobenzenesulfonate, C14H17BrO3S, (II), have been determined. Compound (I) represents the smallesttrans-fused cyclopropane structure known to date, and features the expectedshorteningof the bridging C—C bond relative to the other cyclopropane bond lengths, in contrast to thecis-fused system, (II), where all of the cyclopropane bond lengths are the same. The bicyclic ring system of (I) is disordered across a crystallographi

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2

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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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

Wiberg, Kenneth B., Michael G. Matturro, Paul J. Okarma, et al. "Bicyclo[2.2.0]hex-1(4)-ene." Tetrahedron 42, no. 6 (1986): 1895–902. http://dx.doi.org/10.1016/s0040-4020(01)87609-2.

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5

Dastlik, KA, EL Ghisalberti, BW Skelton, and AH White. "Structural Studies of Bicyclo[3.2.1]octane and Bicyclo[2.2.2]octane Diols." Australian Journal of Chemistry 45, no. 5 (1992): 959. http://dx.doi.org/10.1071/ch9920959.

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The crystal structures of 4 α,5 α and 4 β,5 β-dihydroxyisoeremone (4) and (5), incorporating the bicyclo[2.2.2]octane skeleton, and the bicyclo[3.2.l]octane diol (6) have been determined by X-ray crystallographic methods.

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6

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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7

Montalt, Joaquin, Frédéric Linker, Frédéric Ratel, and Michel Miesch. "Synthesis of Bicyclo[4.n.1]alkanones." Journal of Organic Chemistry 69, no. 20 (2004): 6715–21. http://dx.doi.org/10.1021/jo048923q.

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8

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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9

Yadav, Priya, Shilpa Yadav, Asha Gurjar, and Raj K. Bansal. "Cope Rearrangement in Bicyclo[5.1.0]octa-2,5-diene and its Mono- and Di-Hetero Analogues: A DFT Study." Australian Journal of Chemistry 70, no. 6 (2017): 683. http://dx.doi.org/10.1071/ch16488.

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The Cope rearrangements of bicyclo[5.1.0]octa-2,5-diene and its 4-hetero-(aza/oxa/phospha) and 4,8-dihetero analogues were investigated using density functional theory at the B3LYP/6–31+G* level in gas phase. The rearrangements of bicyclo[5.1.0]octa-2,5-diene and its symmetrical 4,8-dihetero analogues followed a concerted mechanism involving synchronous transition states. In other cases, although a concerted mechanism was observed, asynchronous transition states were involved. In the case of bicyclo[5.1.0]octa-2,5-diene, a degenerate Cope rearrangement was expected to occur at room temperature

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10

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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11

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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12

Pelties, Stefan, Andreas W. Ehlers, and Robert Wolf. "Insertion of phenyl isothiocyanate into a P–P bond of a nickel-substituted bicyclo[1.1.0]tetraphosphabutane." Chemical Communications 52, no. 39 (2016): 6601–4. http://dx.doi.org/10.1039/c6cc01572g.

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A nickel-substituted bicyclo[1.1.0]tetraphosphabutane is obtained by reacting an NHC-based cyclopentadienyl nickel(i) radical with P<sub>4</sub>. The CS and CN bonds of phenyl isothiocyanate insert into a P–P bond of the “P<sub>4</sub> butterfly” skeleton, affording new complexes with a unique bicyclo[3.1.0]heterohexane framework.

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13

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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14

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 (2006): 1167–73. http://dx.doi.org/10.1002/jlac.199619960716.

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15

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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16

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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17

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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18

Lokanath, N. K., D. Revannasiddaiah, M. A. Sridhar, and J. Shashidhara Prasad. "Crystal Structure of 1-Hexyl-4-(4-Isothio-Cyantophenyl) Bicyclo[2,2,2] Octane." Molecular Crystals and Liquid Crystals Science and Technology. Section A. Molecular Crystals and Liquid Crystals 364, no. 1 (2001): 703–10. http://dx.doi.org/10.1080/10587250108025038.

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19

Holl, Ralph, Mareike Dykstra, Martin Schneiders, et al. "Synthesis of 2,5-Diazabicyclo[2.2.2]octanes by Dieckmann Analogous Cyclization." Australian Journal of Chemistry 61, no. 11 (2008): 914. http://dx.doi.org/10.1071/ch08350.

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Starting with (S)-aspartate, methyl (S)-2-[1-allyl-4-(4-methoxybenzyl)-3,6-dioxopiperazin-2-yl]acetate 10 was synthesized in a four-step synthesis. Deprotonation of 10 and subsequent trapping of the first cyclization product led to the bicyclic mixed acetal 13 in 15% yield. The low yield of 13, compared with the yield of the corresponding glutamate derivatives, is explained by the higher energy (strain) of the bicyclo[2.2.2]octane system and the lower conformational flexibility of the shorter acetate side chain. The formation of a six-membered Na+-chelate 12 as intermediate is responsible for

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20

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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21

Maslov, Ivan O., Tatiana V. Zinevich, Olga G. Kirichenko, et al. "Design, Synthesis and Biological Evaluation of Neogliptin, a Novel 2-Azabicyclo[2.2.1]heptane-Based Inhibitor of Dipeptidyl Peptidase-4 (DPP-4)." Pharmaceuticals 15, no. 3 (2022): 273. http://dx.doi.org/10.3390/ph15030273.

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Compounds that contain (R)-3-amino-4-(2,4,5-trifluorophenyl)butanoic acid substituted with bicyclic amino moiety (2-aza-bicyclo[2.2.1]heptane) were designed using molecular modelling methods, synthesised, and found to be potent DPP-4 (dipeptidyl peptidase-4) inhibitors. Compound 12a (IC50 = 16.8 ± 2.2 nM), named neogliptin, is a more potent DPP-4 inhibitor than vildagliptin and sitagliptin. Neogliptin interacts with key DPP-4 residues in the active site and has pharmacophore parameters similar to vildagliptin and sitagliptin. It was found to have a low cardiotoxic effect compared to sitaglipti

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22

Slootweg, J. Chris, Andreas W. Ehlers, and Koop Lammertsma. "ISOMERIZATION OF 2-PHOSPHA-4-SILA-BICYCLO[1.1.0]BUTANE." Phosphorus, Sulfur, and Silicon and the Related Elements 179, no. 4-5 (2004): 803–7. http://dx.doi.org/10.1080/10426500490427187.

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23

Lloyd, Barry A., and Atta M. Arif. "Bicyclo[2.2.1]hept-2-en-7-yl 4-bromobenzoate." Acta Crystallographica Section E Structure Reports Online 68, no. 7 (2012): o2209. http://dx.doi.org/10.1107/s1600536812027882.

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24

BEHRENDT, U., B. GABOR, R. MYNOTT, and H. BUTENSCHOEN. "ChemInform Abstract: Rearrangement of a Bicyclo(3.2.0)hept-2-ene to a Bicyclo(4.1.0)hept-4- ene." ChemInform 27, no. 40 (2010): no. http://dx.doi.org/10.1002/chin.199640056.

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25

Piers, Edward, and Grace L. Jung. "Thermal rearrangement of functionalized 6-exo-(1-alkenyl)bicyclo[3.1.0]hex-2-enes. A total synthesis of (±)-sinularene." Canadian Journal of Chemistry 63, no. 4 (1985): 996–98. http://dx.doi.org/10.1139/v85-167.

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A total synthesis of the racemic form of the marine sesquiterpenoid (−)-sinularene (1) is described. The key step of the synthesis involved the stereoselective thermal rearrangement of the highly functionalized bicyclo[3.1.0]hexene 12 to provide, in 86% yield, the substituted bicyclo[3.2.1]octadiene 13. Conversion of the latter substance into (±)-sinularene (1) was accomplished via an efficient 4-step sequence.

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26

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 (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

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27

Adcock, William, and Dieter Lunsmann. "Effects of Bridgehead Substituents on the Stability of the 1-Norbornyl Radical." Collection of Czechoslovak Chemical Communications 64, no. 10 (1999): 1572–82. http://dx.doi.org/10.1135/cccc19991572.

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The electrochemical reductive cleavage of a series of 4-X-substituted bicyclo[2.2.1]heptan- 1-yl bromides and iodides (X = H, F, Cl, Br, I, SnMe3) was investigated by means of cyclic voltammetry. By application of the dissociative electron-transfer theory, the variations in the peak reduction potentials translate to values for the weakening of the C-Br and C-I bond dissociation energies (∆D) upon replacement of H by all the substituents (X). The ∆D values suggest significant through-space stabilizing interactions (homohyperconjugation) in the 4-X-substituted bicyclo[2.2.1]heptane radical speci

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28

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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29

Wu, Di, Rakesh Ganguly, Yongxin Li, Sin Ni Hoo, Hajime Hirao, and Rei Kinjo. "Reversible [4 + 2] cycloaddition reaction of 1,3,2,5-diazadiborinine with ethylene." Chemical Science 6, no. 12 (2015): 7150–55. http://dx.doi.org/10.1039/c5sc03174e.

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30

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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31

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 (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]o

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32

Koppel, I. A., M. Mishima, L. M. Stock, R. W. Taft, and R. D. Topsom. "Acidities of 4-substituted benzoic, bicyclo[2.2.2]oct-1-yl and bicyclo[2.2.2]oct-2-enyl carboxylic acids." Journal of Physical Organic Chemistry 6, no. 12 (1993): 685–89. http://dx.doi.org/10.1002/poc.610061205.

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33

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

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34

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

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35

Aydogan, Abdullah, and Ahmet Akar. "Tetrakis(bicyclo[2.2.2]oct-2-ene)-Fused Calix[4]pyrrole." Helvetica Chimica Acta 97, no. 10 (2014): 1427–32. http://dx.doi.org/10.1002/hlca.201400009.

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36

Lauro, Figueroa-Valverde, Rosas-Nexticapa Marcela, Lopez-Ramos Maria, et al. "Synthesis of a New Dioxaspiro[bicyclo[3.3.1]nonane-oxabicyclo[6.2.0]deca- 1(10),8-dien-4-one Derivative Using Some Chemical Strategies." Letters in Organic Chemistry 17, no. 5 (2020): 393–402. http://dx.doi.org/10.2174/1570178617666191116123359.

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There are several protocols for the preparation of bicyclic derivatives; however, some methods use dangerous and require special conditions. The aim of this study was to synthesize a new Dioxaspiro[ bicyclo[3.3.1]nonane-oxabicyclo[6.2.0]-deca-1(10), 8-dien-4-one (compound 8). Compound 8 was prepared using some reactions such as; i) etherification, ii) reduction, iii) amidation, iv) imination and v) 2+2 addition. The chemical structure of 8 and its intermediaries were completely characterized by spectroscopic techniques and elemental analysis. The synthesis showed a yield of 85% for compound 8.

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Saunders, James, Chris Adamson, Yumeela Ganga-Sah, Andrew R. Lewis, and Andrew J. Bennet. "Rearrangement and nucleophilic trapping of bicyclo[4.1.0]hept-2-yl derived nonclassical bicyclobutenium ions." Canadian Journal of Chemistry 96, no. 2 (2018): 235–40. http://dx.doi.org/10.1139/cjc-2017-0569.

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Here we describe the synthesis of two specifically labelled 13C isotopologues of cis-2-(4-nitrophenoxy)bicyclo[4.1.0]heptane and their solvolysis reactions in trifluoroethanol. By using one- and two-dimensional 1H- and 13C-NMR spectroscopy, we characterized the pathways for the rearrangement of these isotopologues to give 13C-labelled 4-(2,2,2-trifluoroethoxy)cycloheptene. We show that the initially formed cationic intermediate undergoes a degenerate rearrangement, which does not reach equilibrium before nucleophilic capture of the cation. Moreover, we show that the nonclassical carbocation, c

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38

Verma, Sharad K., Que H. Nguyen, James M. MacDougall, Everly B. Fleischer, and Harold W. Moore. "Oxy-Cope Rearrangements of Bicyclo[3.2.0]heptenones. Synthesis of Bicyclo[4.2.1]non-1(4)-en-6-ones and Bicyclo[5.2.1]dec-1(10)-en-5-ones." Journal of Organic Chemistry 65, no. 11 (2000): 3379–86. http://dx.doi.org/10.1021/jo991765w.

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39

Plougastel, Lucie, Oleksandr Koniev, Simon Specklin, et al. "4-Halogeno-sydnones for fast strain promoted cycloaddition with bicyclo-[6.1.0]-nonyne." Chem. Commun. 50, no. 66 (2014): 9376–78. http://dx.doi.org/10.1039/c4cc03816a.

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40

Bauri, A. K., Sabine Foro, and Nhu Quynh Nguyen Do. "Crystal structure of a bioactive sesquiterpene isolated fromArtemisia reticulata." Acta Crystallographica Section E Crystallographic Communications 72, no. 4 (2016): 460–62. http://dx.doi.org/10.1107/s2056989016003236.

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The title compound, C15H24O2{systematic name: 1-[6-hydroxy-7-(propan-2-yl)-4-methylidene-2,3,3a,4,5,6,7,7a-octahydro-1H-inden-1-yl]ethanone} was isolated fromA. reticulataby column chromatography over silica gel by gradient solvent elution. The molecule comprises a bicyclo[4.3.0]nonane ring bearing acetoxy, hydroxy and isopropyl substituents, and an exocyclic double bond on the cyclohexane ring. In the bicyclic skeleton, the cyclohexane ring adopts a chair conformation ring and the cyclopentane ring is in an envelope conformation. In the crystal, molecules are linked by O—H...O hydrogen bonds,

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41

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 (2001): 6943–57. http://dx.doi.org/10.1021/jo010269g.

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42

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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43

Fu, Jian-Guo, Yi-Fan Shan, Wang-Bin Sun, Guo-Qiang Lin, and Bing-Feng Sun. "An asymmetric approach to bicyclo[2.2.1]heptane-1-carboxylates via a formal [4 + 2] cycloaddition reaction enabled by organocatalysis." Organic & Biomolecular Chemistry 14, no. 23 (2016): 5229–32. http://dx.doi.org/10.1039/c6ob00814c.

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An organocatalytic formal [4 + 2] cycloaddition reaction has been developed that permits rapid access to bicyclo[2.2.1]heptane-1-carboxylates with excellent enantioselectivities under mild and operationally simple conditions.

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44

Puviarasan, K., L. Govindasamy, D. Velmurugan, et al. "3-Phenylspiro[bicyclo[2.2.1]hept-5-ene-2,3'-chroman]-4'-one." Acta Crystallographica Section C Crystal Structure Communications 54, no. 7 (1998): 961–63. http://dx.doi.org/10.1107/s0108270198000110.

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45

Watson, W. H., and A. Nagl. "7,7-Dichloro-4-(diphenylmethylene)bicyclo[3.2.0]hept-2-en-6-one." Acta Crystallographica Section C Crystal Structure Communications 43, no. 12 (1987): 2463–65. http://dx.doi.org/10.1107/s0108270187087328.

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46

Ebby, N., J. Lapasset, L. Pizzala, J. P. Aycard, and H. Bodot. "Diméthyl-1,6 oxa-7 bicyclo[4.1.0]heptanedicarbonitrile-3-trans,4-cis." Acta Crystallographica Section C Crystal Structure Communications 43, no. 7 (1987): 1417–20. http://dx.doi.org/10.1107/s0108270187091650.

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47

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 (2001): 6932–42. http://dx.doi.org/10.1021/jo010268o.

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48

Adcock, William, Gaik B. Kok, V. Sankar Iyer, Dennis G. Peters, Kristin M. Lundy, and William Kitching. "Polar substituent effects in the bicyclo[2.2.2]octane ring system: polarography of 4-substituted bicyclo[2.2.2]oct-1-yl iodides." Journal of Organic Chemistry 51, no. 4 (1986): 564–67. http://dx.doi.org/10.1021/jo00354a036.

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Bauman, Danuta, Aldona Wasik, and Jan Jadzyn. "Intermolecular interactions in mixtures of dichroic dyes withn-alkyl-4-(4-isothiocyanatophenyl)bicyclo[2,2,2]octanes." Liquid Crystals 20, no. 2 (1996): 195–200. http://dx.doi.org/10.1080/02678299608031126.

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Raghunathan, V. A., A. P. Divya, M. S. Madhava, D. Revannasiddaiah, and R. Somashekar. "Orientational Order Parameter in 1-Hexyl-4-(4-Isothiocyanatophenyl) Bicyclo [2,2,2] Octane using X-Rays." Molecular Crystals and Liquid Crystals Science and Technology. Section A. Molecular Crystals and Liquid Crystals 365, no. 1 (2001): 883–87. http://dx.doi.org/10.1080/10587250108025368.

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