139458-87-0

Upstream product

• 18165-76-9 trimethylsilanyl-methanethiol 
• 2651-15-2 N-[bis(methylthio)methylene]-p-toluenesulfonamide 
• 6503-22-6 S-methyl N-(p-toluenesulfonyl)dithioiminocarbonate 
• 2344-80-1 Chloromethyltrimethylsilane 
• 139474-76-3 S,S'-Bis(trimethylsilylmethyl) N-(p-toluenesulfonyl)dithioiminocarbonate 

Downstream Products

• 16245-83-3 2-(4-methylphenyl)thiirane 
• 1498-99-3 styrenesulfide 
• 6388-69-8 2-(4-methoxyphenyl)thiirane 
• 139458-90-5 2-(3-methoxyphenyl)thiirane 
• 139458-91-6 2-(2-methoxyphenyl)thiirane 
• 3435-51-6 4-ethenylbenzonitrile 
• 100-13-0 4-nitrostyrene 
• 139458-92-7 2-(2,6-dichlorophenyl)thiirane 
• 139458-93-8 2-(4-phenylphenyl)thiirane 
• 139458-89-2 2-(2-methylphenyl)thiirane 

Relevant 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

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

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