Trifluoroacetic acid in the synthesis of thiolcarbamates and s-methyl alkanethioates

The major products of the reaction of 2-bromohexanoic acid with methyl thiocyanate in trifluoroacetic acid are S-methyl 2-bromohexanethioate (II) (55% yield), S-methyl 2,2,2-trifluoroethanethioate (IV) (31% yield), N-trifluoro-acetyltrifluoroacetamide (V) (11% yield), and N-trifluoroacetyl-S-methylthiol-carbamate (III) (29% yield). N-2-Bromohexanoyl-S-methylthiolcarbamate (I), N-2-bromohexanoyltrifluoroacetaraide (VI), 2-thiapropioamide(VII), and S-methyl hex-anethioate (VIII) are also formed in minor amounts.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 1, pp. 195–198, January, 1991.