41469-78-7

Basic information

• Product Name: S-(tert-butyl)-S-methyl-N-(p-tolylsulfonyl)sulfilimine
• Synonyms: S-(tert-butyl)-S-methyl-N-(p-tolylsulfonyl)sulfilimine
• CAS NO: 41469-78-7
• Molecular Weight: 273.42
• Mol File: 41469-78-7.mol

Chemical Properties

• CAS DataBase Reference: S-(tert-butyl)-S-methyl-N-(p-tolylsulfonyl)sulfilimine(CAS DataBase Reference)
• NIST Chemistry Reference: S-(tert-butyl)-S-methyl-N-(p-tolylsulfonyl)sulfilimine(41469-78-7)
• EPA Substance Registry System: S-(tert-butyl)-S-methyl-N-(p-tolylsulfonyl)sulfilimine(41469-78-7)

Safety Data

• Hazardous Substances Data: 41469-78-7(Hazardous Substances Data)

Upstream product

• 6163-64-0 tert-butyl methyl sulphide 
• 127-65-1 chloroamine-T 

Relevant articles and documents

A simple method for the preparation of N-sulfonylsulfilimines from sulfides

While excellent methods exist for the oxidation of sulfides to sulfoxides R1R2S → R1R2SO, the aza-version of this atom transfer redox process, i.e., R1R2S → R1R2S=N-SO

Experimental and Computational Studies of the Structure of Sulfonimidoyl Vinyllithiums

tBuCH=C(Li)S(O)(NSO2Tol)Ph?L (L=2THF, TMEDA) (1?L) in THF solution is a monomer with a C?Li bond according to NMR spectroscopy and cryoscopy. It was identified as CIP through the scalar 13C,6Li coupling and 6Li,{1H} NOE experiments. The CIP has a six-membered C-Li-O-S-N-S chelate ring structure. 6Li,1H FUCOUP and 6Li,1H HMQC NMR experiments of 1?TMEDA revealed a scalar 6Li,1H coupling across the Li?C=C?H bonds. According to the NMR data the π-bond of 1?L is polarized by the negative charge of the anionic C atom. tBuCH=C(Li)S(O)(NMe)Ph (2?L) is most likely also a monomer with a C?Li bond. According to 6Li,{1H} NOE experiments it has a four-membered C-Li-N-S chelate ring structure. 13C NMR spectroscopy showed the C?Li bonds of 1?L and 2?L to be fluxional. 1H NMR spectroscopy and 1D TOCSY experiments of Ph2C=C(Li)S(O)(NSO2Tol)Ph revealed topomerization of the phenyl groups, which is attributed to a fast positional exchange of the Li atom and the sulfonimidoyl group. The fluxionality of the C?Li bond and the interchange of the Li atom and the sulfonimidoyl group at the anionic C atom of sulfonimidoyl vinyllithiums, which result in a low configurational stability, most likely involve the formation of O,Li and N,Li CIPs through heterolysis of the C?Li bond. Ab initio calculation of MeCH=C(Li)S(O)(NMe)Ph yielded an energy minimum structure with a C?Li bond, a four-membered C-Li-N-S chelate ring and a strongly expanded C=C?Li bond angle. According to calculation of MeCH=C(Li)S(O)(NMe)Ph, [MeCH=CS(O)(NMe)Ph]? and MeCH=C(H)S(O)(NMe)Ph deprotonation is not accompanied by a shortening of the C?S bond. Ab initio calculation of MeCH=C(Li)S(O)(NSO2Me)Ph gave a structure with a C?Li bond and a six-membered C-Li-O-S-N-S chelate ring. 6Li,1H NOE experiments and cryoscopy of LiCH2S(O)(NSO2Tol)Ph (3) revealed a monomeric CIP with a C?Li bond. The CIP has a six-membered C-Li-O-S-N-S chelate ring structure found in polymeric 3 in the crystal.