184705-46-2Relevant academic research and scientific papers
Efficient one-pot synthesis of 1-chlorovinyl p-tolyl sulfoxides from aldehydes and ketones by the Horner-Wadsworth-Emmons reaction
Kimura, Tsutomu,Kobayashi, Gen,Ijima, Shiori,Saito, Sae,Imafuji, Aki,Satoh, Tsuyoshi
, (2017/10/27)
A variety of 2-monosubstituted and 2,2-disubstituted 1-chlorovinyl p-tolyl sulfoxides was synthesized through a one-pot procedure by the Horner-Wadsworth-Emmons reaction of carbonyl compounds with [chloro(diethoxyphosphoryl)(p-tolylsulfinyl)methyl]lithium, which was generated from diethyl chlorophosphate, chloromethyl p-tolyl sulfoxide, and lithium diisopropylamide in advance. The in situ-prepared sulfoxides were directly converted into alkynes via the sulfoxide/magnesium exchange reaction with i-PrMgCl and the subsequent Fritsch-Buttenberg-Wiechell rearrangement of the resulting magnesium alkylidene carbenoids.
A synthesis of di- and tri-substituted β,γ-unsaturated esters from aldehydes by the magnesium carbenoid 1,2-CH and 1,2-CC insertion as the key reaction
Yamashita, Hironori,Satoh, Tsuyoshi
scheme or table, p. 613 - 627 (2009/04/06)
Addition reaction of 1-chlorovinyl p-tolyl sulfoxides, which were derived from aldehydes, with lithium enolate of tert-butyl acetate at -78 °C in THF gave adducts in high yields. Treatment of these adducts with Grignard reagents resulted in the formation
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.
