139474-76-3Relevant academic research and scientific papers
N-bis(methylthio)methylene derivatives. VII. Syntheses and reactions of synthetic equivalents of new 1,3-dipolar reagents using N- bis(methylthio)methylene derivatives
Tominaga,Ogata,Ueda,Kohra,Hosomi
, p. 1425 - 1434 (2007/10/03)
N-Cyano- or N-(p-toluenesulfonyl)-N'-(trimethylsilylmethyl)-S- methylisothioureas (3,4), readily prepared by reactions of S,S'-dimethyl N- cyano- (1a) and S,S'-dimethyl N-(p-toluenesulfonyl)- (1b) carbonimidodithioates with trimethylsilylmethylamine (2a), followed by N- alkylation, have been found to provide synthetic equivalents of iminoazomethine ylide. Treatment of these compounds with cesium fluoride in the presence of reactive heterodipolarophiles such as carbonyl compounds afforded 1,3-dipolar cycloadducts, 4,5-dihydro-2-iminooxazoles and 4,5- dihydro-2-iminothiazoles, via the 1,3-elimination of (methylthio)trimethylsilane. S-Methyl-S'-trimethylsilylmethyl N-cyano- (5a) and N-(p-toluene-sulfonyl)- (5b) carbonimidodithioates, also readily prepared from the corresponding 1a and 1b with (mercaptomethyl)trimethylsilane (2b), were used as new reagents for introducing a thioformaldehyde unit at a carbonyl carbon. Reactions of these compounds with aldehydes in the presence of cesium fluoride afforded thiiranes via the 1,3-dipolar cycloaddition of iminothiocarbonyl ylide to the C=O double bond. Reactions of 5 with dimethyl fumarate and maleate in the presence of cesium fluoride in acetonitrile gave 1,3-dipolar cycloadducts, dimethyl 2-(N-(p- toluenesulfonyl)imino)tetrahydrothiophene-3,4-dicarboxylates.
New synthesis of thiiranes by fluoride ion-promoted reaction of S-methyl-S'-trimethylsilylmethyl N-(p-toluenesulfonyl)dithioiminocarbonate and 2-(trimethylsilylmethylthio)thiazoline with aldehydes
Tominaga,Ueda,Ogata,Kohra,Hojo,Ohkuma,Tomita,Hosomi
, p. 85 - 88 (2007/10/02)
The title compounds, readily prepared by the reaction of the corresponding S-methyl N-(p-toluene-sulfonyl)dithioiminocarbonate and 2-mercaptothiazoline with (chloromethyl)trimethylsilane in the presence of a base, were used as a new reagents for the intro
