Reaction of Enol Ethers with Carbenes. X. Ring Opening of 2,2-Dichlorocyclopropyl Phenyl Sulfides
- 1 February 1972
- journal article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 45 (2) , 509-515
- https://doi.org/10.1246/bcsj.45.509
Abstract
The ring opening reactions of six known or new 2,2-dichlorocyclopropyl phenyl sulfides have been carried out with potassium t-butoxide in t butyl alcohol and with pyridine. The products were enynes, butadienes, allenes and, as minor products, α,β-unsaturated aldehydes containing the phenylmercapto group. Reaction of a mixture of cis- and trans-1,1-dichloro-2-methyl-3-phenylmercaptocyclopropane (2) with pyridine gave unchanged trans-isomer. This apparent selectivity is explained on the basis of the steric effects for ring opening.Keywords
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