TRIFLUOROACETIC ACID IN THE SYNTHESIS OF THIOLCARBAMATES AND S-METHYL ALKANETHIOATES

Article abstract of DOI:10.1007/BF00959656

The major products of the reaction of 2-bromohexanoic acid with methyl thiocyanate in trifluoroacetic acid are S-methyl 2-bromohexanethioate (II) (55percent yield), S-methyl 2,2,2-trifluoroethanethioate (IV) (31percent yield), N-trifluoroacetyltrifluoroacetamide (V) (11percent yield), and N-trifluoroacetyl-S-methylthiolcarbamate (III) (29percent yield).N-2-Bromohexanoyl-S-methylthiolcarbamate (I), N-2-bromohexanoyltrifluoroacetamide (VI), 2-thiapropioamide (VII), and S-methyl hexanethioate (VIII) are also formed in minor amounts.