128098-87-3

Upstream product

• 128098-82-8 (3RS,4RS)-2,4-dimethyl-3,5,5-tris(phenylthio)octan-2-ol 
• 931-59-9 benzenesulfenyl chloride 
• 882-33-7 diphenyldisulfane 
• 128098-70-4 methyl (2RS,3RS)-3-methyl-2,4,4-tris(phenylthio)heptanoate 
• 64269-39-2 1-[bis(phenylthio)methyl]propane 
• 85020-99-1 methyl α-phenylthiobut-2-enoate 

Relevant academic research and scientific papers

Phenylthio Migrations in the Rearrangement of 2,4,4-Tris(phenylthio)butanols

2,4,4-Tris(phenylthio)butanols rearranged by a -PhS shift to give and E,Z mixture of vinyl sulfides with thionyl chloride but only the Z isomer with toluene-p-sulfonic acid.The -PhS shift occured only if another PhS group was present β to the hydroxyl group.The mechanism and scope of the reaction and the preparation of 2,4,4-tris(phenylthio)butanols via Michael addition of dithioacetal nucleophiles to methyl crotonate followed by α-sulfenylation is reported.

PHENYLTHIO SHIFTS OF 2,4,4-TRISPHENYLTHIOBUTANOLS

The title compounds (1) undergo a -PhS shift to give an E,Z mixture of vinyl sulphides (2) with thionyl chloride but only the Z isomer if toluene-p-sulphonic acid is used.The reaction occurs only if another PhS group is present β to the hydroxyl.The