67965-36-0Relevant academic research and scientific papers
Preparation of 2-chlorobuta-1,3-dienes by dichlorocyclopropanation of allylsilanes followed by desilylation
Mitani, Michiharu,Kobayashi, Yoshinori,Koyama, Kikuhiko
, p. 653 - 656 (2007/10/02)
Allylsilanes react with dichlorocarbene to form dichloropropanes which, in turn, afford 2-chlorobuta-1,3-dienes when treated with cesium fluoride in DMF under reflux.The Z stereochemistry of the products differs from that of the starting allylsilanes.Lengthy reaction times were necessary to induce desilylation because of the lack of steric congestion in the intermediate silylmethyl-substituted cyclopropanes. 5-Methyl-7-trimethylsilylhepta-1,5-diene was cyclopropanated regioselectively at the inner ene function in spite of unfavourable steric congestion, possibly as a result of the electron-donating effect of the allylic silyl group induced by the ?-? conjugation.
