94741-87-4Relevant academic research and scientific papers
A + + 4> Polar Cycloaddition of α-Thiocarbocations with 1,3-Dienes: Synthesis and Thermal Reaction of 1-Acyl-1-methylthio-2-vinylcyclopropanes
Ishibashi, Hiroyuki,Okada, Motofumi,Nakatani, Hiroshi,Ikeda, Masazumi,Tamura, Yasumitsu
, p. 1763 - 1768 (2007/10/02)
Treatment of methyl 2-chloro-2-(methylthio)acetate, 1-chloro-1-(methylthio)propan-2-one, chloro(methylthio)methyl phenyl ketone, or 2-chloro-2-(methylthio)acetonitrile with 1,3-dienes in the presence of stannic chloride followed by addition of triethylamine gave 1-acyl- or 1-cyano-1-(methylthio)-2-vinylcyclopropanes.A mechanistic interpretation of this reaction is presented.Thermal behaviour of the vinylcyclopropanes is also described.
A ++4> POLAR CYCLOADDITION OF α-CHLOROSULFIDES WITH CONJUGATED DIENES: ONE-POT SYNTHESIS OF 1-ACYL- AND 1-CYANO-1-METHYLTHIO-2-VINYLCYCLOPROPANES
Ishibashi, H.,Kitano, Y.,Nakatani, H.,Okada, M.,Ikeda, M.,et al.
, p. 4231 - 4232 (2007/10/02)
In the presence of SnCl4, methoxycarbonyl-, acetyl-, benzoyl-, or cyano-substituted chloromethyl methyl sulfide (1-4) undergoes ++4> polar cycloaddition with conjugated dienes to afford the cycloadducts of type 7, which, on treatment with base, are converted into the 1-acyl- or 1-cyano-1-methylthio-2-vinylcyclopropanes 9-10 via the ylide intermediates of type 8.
