105961-79-3Relevant academic research and scientific papers
SYNTHESIS OF GEM-DISUBSTITUTED ETHYLENE AND ACETYLENE DERIVATIVES OF THE CYCLOPROPANE SERIES BASED ON 1,1-DIACYLCYCLOPROPANES
Zefirov, N. S.,Kozhushkov, S. I.,Kuznetsova, T. S.,Gleiter, R.,Eckert-Maksic, M.
, p. 95 - 105 (2007/10/02)
Methods for the conversion of 1,1-diacylcyclopropanes into gem-disubstituted dienes and acetylenes of the cyclopropene series were investigated: a) Reduction followed by dehydration of the diols; b) conversion of the diketones into bistosylhydrazones and treatment of the latter with methyllithium; c) dehydrohalogenation of gem-di(1-halogenoalkyl)cyclopropanes by the action of bases.Dehydration leads to intramolecular nucleophilic opening of the three-membered ring. 1,1-Divinylcyclopropanes and stereoisomeric 1,1-di(1-propenyl)cyclopropanes were obtained by two different methods, and the corresponding diynes and enynes were synthesized from them by bromination followed by dehydrobromination. 1,1-Di(1-propynyl)cyclopropane can be obtained by alkylation of 1,1-diethynylcyclopropane and also directly from 1,1-divinylcyclopropane without isolation of the intermediate 1,1-diethynylcyclopropane.
