Organic reaction in water. Part 3: Diastereoselectivity in Michael additions of thiophenol to nitro olefins in aqueous media

Authors
da Silva, FM Jones, J
Citation
Fm. Da Silva et J. Jones, Organic reaction in water. Part 3: Diastereoselectivity in Michael additions of thiophenol to nitro olefins in aqueous media, J BRAZ CHEM, 12(2), 2001, pp. 135-137
Citations number
20
Categorie Soggetti
Chemistry
Journal title
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY
ISSN journal
01035053 → ACNP
Volume
12
Issue
2
Year of publication
2001
Pages
135 - 137
Database
ISI
SICI code
0103-5053(2001)12:2<135:ORIWP3>2.0.ZU;2-#
Abstract
Thiophenol reacts with nitro olefins in aqueous media to give the correspon ding nitro-sulfides in 58-95% yield. This procedure results in selective fo rmation of the anti products. In the case of the cyclic nitro olefin 1-nitr o-cyclohexene the only product observed was the cis-1-nitro-2-(phenylthio)c yclohexane. This methodology is of interest due to the use of water as solv ent, thus minimizing the cost, the operational hazards and environmental po llution.