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- Title
Reaction of 1-bromovinyl and 1-bromo-2-phenylvinyl sulfones with some CH acids.
- Authors
Vasin, V.; Bolusheva, I.; Kalyazin, V.; Razin, V.
- Abstract
Benzyl, methyl, and phenyl α-bromovinyl sulfones reacted with malononitrile and dimethyl malonate sodium enolates in THF to give sulfonyl-substituted cyclopropanes. Reactions of the same sulfones with methyl acetoacetate sodium enolate afforded the corresponding sulfonyl-substituted cyclopropanes as mixtures of cis and trans isomers with a small impurity of 5-sulfonyl-4,5-dihydrofuran derivative. Phenyl and p-tolyl 1-bromo-2-phenylvinyl sulfones reacted with methyl acetoacetate sodium salt to produce a mixture of trans-isomeric 5-sulfonyl-4,5-dihydrofuran and Michael adduct of the CH acid with activated acetylene generated by concurrent 1,2-dehydrobromination of the initial α-bromovinyl sulfone.
- Subjects
SULFONES; MICHAEL reaction; MALONONITRILE; PHENYL compounds; DEHYDROBROMINATION; ACETOACETIC acid; CHEMICAL reactions
- Publication
Russian Journal of Organic Chemistry, 2014, Vol 50, Issue 10, p1448
- ISSN
1070-4280
- Publication type
Article
- DOI
10.1134/S1070428014100091