184705-44-0Relevant academic research and scientific papers
Reaction of 1-chlorovinyl p-tolyl sulfoxides with carbanion of acetonitrile: A novel synthesis of cyclopentanone derivatives with three consecutive carbon-carbon bond-formations via the enaminonitriles
Satoh, Tsuyoshi,Ota, Hiroyuki
, p. 5113 - 5122 (2007/10/03)
Treatment of 1-chlorovinyl p-tolyl sulfoxides derived from ketones with cyanomethyllithium gave cyclopentadienyl enaminonitriles in high yields with three consecutive carbon- carbon bond-formations. However, the 1-chlorovinyl p-tolyl sulfoxides derived from aldehydes did not give good results. The mechanism of this reaction and the reaction of the enaminonitriles to convert cyclopentanone derivatives were investigated. Several α-carbanion of nitriles other than acetonitrile added to the 1-chlorovinyl p-tolyl sulfoxides at low temperature in good yield; however, they did not cyclize upon warming to room temperature. (C) 2000 Elsevier Science Ltd.
Stereoselective Horner-Wittig synthesis of (Z)-1-chlorovinyl sulfoxides
Otten, Pieter A.,Davies, Honorine M.,Van Steenis, Jan Hein,Gorter, Syb,Van Der Gen, Arne
, p. 10527 - 10544 (2007/10/03)
This paper describes the synthesis of (Z)-1-chlorovinyl sulfoxides 1 by the Horner-Wittig reaction. The required [(α-chloro)sulfinylmethyl]diphenylphosphine oxides 2 (R1=Me, c-Hex, Ph, p-Tol, p-(CF3)Ph), were prepared in high yields
A Horner-Wittig synthesis of 1-chlorovinyl sulfoxides
Otten,Davies,Van Der Gen
, p. 449 - 452 (2007/10/03)
1-Chlorovinyl sulfoxides 1 were prepared by Horner-Wittig reaction of the readily accessible [(α-chloro)sulfinylmethyl)diphenylphosphine oxides 2 with aldehydes. Excellent Z-selectivity was observed in most cases.
