2031-18-7

Upstream product

• 4104-47-6 N-sulfinyl-p-toluenesulfonamide 
• 78-79-5 isoprene 
• 556-82-1 3-methyl-2-buten-1-ol 
• 115-18-4 2-methyl-3-buten-2-ol 

Downstream Products

• 33403-66-6 (Z)-2-Methyl-4-(toluene-4-sulfonylamino)-but-2-ene-1-sulfinic acid methyl ester 
• 39551-13-8 4,5-epoxy-5-methyl-2-(toluene-4-sulfonyl)-[1,2]thiazinane 1,1-dioxide 
• 2080-62-8 4-methyl-N-(3-methylbut-3-en-1-yl)benzenesulfonamide 
• 33303-29-6 N-((Z)-4-Methanesulfonyl-3-methyl-but-2-enyl)-4-methyl-benzenesulfonamide 
• 153633-33-1 3-methyl-1-(4-methylbenzenesulphonyl)-1H-pyrrole 

Relevant academic research and scientific papers

N-p-Toluenesulfonylpyrroles from 1,3-dienes

1,3-Dienes can be converted to N-p-toluenesulfonylpyrroles in two steps: 1) [4+2]-cycloaddition with N-sulfinyl-p-toluenesulfonamide and 2) conversion of the 3,6-dihydro-1,2-thiazine oxide adduct to a pyrrole using triethylamine-trimethylphosphite.

REACTIONS OF N-SULFINYL-p-TOLUENESULFONAMIDE WITH ALCOHOLS

N-Sulfinyl-p-toluenesulfonamide (1) reacted with triaryl- and diarylmethanols to give predominantly N-substituted sulfonamides and SO2 presumably via carbonium ion intermediates.When carbonium ion forming alcohols, such as t-BuOH and Ph2C(Me)OH, were used, the predominant products were alkenes and p-toluenesulfonamide.Allylic alcohols afforded N-substituted sulfonamides, along with dienes and p-toluenesulfonamide.Alcohols wich could not predictably give relatively stable intermediate carbonium ions, gave either dialkyl sulfites or dialkyl ethers, along with p-toluenesulfonamide.In one case, namely with 9-phenylfluorenol, the 1:1 adduct with 1 (an amidosulfite) was isolated.A mechanism for the reaction is proposed.