Perfluoro-1-(butylimino)butyl isothiocyanate. Synthesis and reaction with n-propylamine

Abstract

The reaction of perfluoro-5-azanon-4-ene with KSCN in an aprotic dipolar solvent provides perfluoro-1-(butylimino)butyl isothiocyanate. The latter was reacted with n-propylamine in the presence of triethylamine to obtain fluoro-substituted derivatives of thiourea, heptafluoropropionic acid, and 1,3,5-thiadiazine.

Synthesis of trifluoromethylated heterocycles using partially fluorinated epoxides

“…Perfluorinated isothiocyanates 25 [29][30][31] and 26 [32] readily prepared by the reaction of perfluoro(2-methyl)pentene-2 [33,34] or perfluoro-4-aza-nonene-3 [35,36] with sodium thiocyanate were used for the synthesis of a variety of fluorinated heterocycles (see Refs. [37][38][39][40][41][42][43][44][45][46][47][48] and [32] for reactions of 25 for 26, respectively).…”

“…[37][38][39][40][41][42][43][44][45][46][47][48] and [32] for reactions of 25 for 26, respectively). In this study it was shown that both 25 and 26 (generated in situ by reaction with KSCN in DMF, Scheme 17) rapidly react with 2 giving of the corresponding cyclic imines 25a and 26a, respectively.…”