2505-06-8Relevant academic research and scientific papers
Cyclisation of 5-Bromomethyl-cycloheptene and -cyclo-octene: a New Route to Bicyclooctanes and Bicyclononanes
MacCorquodale, Finlay,Walton, John C.
, p. 347 - 352 (1989)
Reduction of 5-(bromomethyl)cycloheptene with tributyltin hydride gave bicyclooctane; similar reduction of 5-(bromomethyl)cyclo-octene gave bicyclononane together with some bicyclononane.The cyclohept-4-enylmethyl radical intermediate
Generation of cycloheptyne during the solvolysis of cyclohexylidenemethyliodonium salt in the presence of base
Fujita, Morifumi,Ihara, Kenji,Kim, Wan Hyeok,Okuyama, Tadashi
, p. 1849 - 1855 (2007/10/03)
Solvolysis of 4-methylcyclohexylidenemethyl(phenyl)iodonium tetrafluoroborate (1) and its R isomer (69% ee) was carried out in 2,2,2-trifluoroethanol (TFE) and 1,1,1,3,3,3-hexafluoropropan-2-ol (HFP) in the presence of bases such as acetate, pyridine, triethylamine, and alkoxide. The reaction is much faster in TFE than in HFP. Products in TFE include solely un-rearranged (racemized) enol ether 2 together with iodobenzene, while the main product in HFP is ring-expanded (partially racemized) 1-alkoxycycloheptene 3. Results show that 2 is formed via α-elimination with alkylidenecarbene as an intermediate, while the reaction in HFP to give 3 involves a cycloheptyne intermediate that is mostly derived from an intermediate cyclohept-1-enyl cation via the E1-type pathway.
Formation of Bicyclooctane, Bicyclononane, and Bicyclononane by Transannular Radical Cyclisations
MacCorquodale, Finlay,Walton, John C.
, p. 1456 - 1457 (2007/10/02)
Cyclohept-4-enylmethyl radicals undergo transannular cyclisation to give bicyclooctane; likewise, bicyclononane and bicyclononane are obtained from cyclo-oct-4-enylmethyl radicals.
