Synthesis of CarbothioateS-Ester Derivatives Using CarbonochloridothioateS-Esters

Synthesis and rearrangement of glycidic thiol esters. Migratory aptitudes

“…Found: C, 76.03; , 5.12; N, 11.84. Rearrangement of 4d. Using the same procedure 4d was converted to S-phenyl 3,3-dimethyl-3-phenylthiolpyruvate (14), which was obtained as a thick yellow oil that crystallized on standing. Recrystallization (n-hexane and benzene) gave the pure thiolpyruvate 14 as yellow plates in 70% yield: mp 47-48°; NMR (CCI4) 7.18 (s, 10 ), 1.58 (s, 6 H); ir (KBr) 1715,1695 cm-1.…”

“…S-Phenyl 3,3-Dimethyl-3-phenylthiolpyruvate (14). Using the Sphenyl thiolchlorocarbonate procedure described for the synthesis of S-phenyl 3,3-diphenylthiolglycidate (4c), pyruvate salt 15 was converted to thiolpyruvate 14 in 59% yield after column chromatography.…”

ChemInform Abstract: Facile “One‐Pot” Preparation of Phosphonothiolformates. Useful Reagents for the Synthesis of Carbamoylphosphonates.

“…It is particularly noteworthy that the chlorothiol-formate compounds (A) formed in situ can also be isolated by simple distillation under vacuum. 17 Chlorothiolformates (A) are acylating and thiolating reagents 18 of choice towards the synthesis of Glyphosate and its derivatives. 19…”