539791-03-2Relevant academic research and scientific papers
Preparation of oxocanes by electrophilic cyclizations of unsaturated alcohols in the presence of bis(collidine)halonium(I) hexafluorophosphates
Mendes, Christelle,Renard, Sylvie,Rofoo, Mazin,Roux, Marie-Claude,Rousseau, Gerard
, p. 463 - 471 (2007/10/03)
7-Octen-1-ols substituted in the sp3-sp3 carbon chain with carbocyclic (phenyl and cyclopropane) and heterocyclic (epoxide and dioxolane) moieties were prepared and their cyclizations in the presence of bis(collidine)iodonium(I) and-bromonium(I) hexafluorophosphates as electrophiles were studied. Oxocanes were obtained in modest to good yields when a rigid cyclic moiety (cyclopropane or phenyl) was present in the chain, while yields of cyclizations were lower if the cyclic component had a certain flexibility (dioxolane). Low yields were obtained with substrates bearing an epoxide substituent, probably because of stability problems due to the presence of collidine. With the vinylcyclopropane alcohol 12 we observed mainly the opening of the cyclopropane ring and the cyclization produced a tetrahydropyran derivative. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
