142330-26-5Relevant articles and documents
Reactions of Trichloroacetyl Isothiocyanate with Organic Azides
L'abbe, Gerrit,Bosman, Joris,Toppet, Suzanne
, p. 17 - 23 (2007/10/02)
Benzyl azide reacts with trichloroacetyl isothiocyanate to give 7a in chloroform solution, and 11 in acetone solution.These 1,2,4-oxathiazolidines were characterized by 13C nmr spectroscopy (Scheme 2), but could not be isolated since they deteriorated via the carbodiimide 8a into the 1,2,4-thiadiazolidine 9a.The oxathiazoline 6a is assumed as an intermediate and was trapped by isocyanates and dicyclohexylcarbodiimide to give the 1,2,4-thiadiazolidines 10a,b and 12 respectively.Isopropyl azide also reacts with trichloroacetyl isothiocyanate to give the labile oxathiazolidine 7b, which decomposes to the carbodiimide 8b and the 1,2,4-thiadiazolidine 9b.In the case of diphenylmethyl azide, however, no evidence was obtained for the presence of the oxathiazolidine 7c in the 1H nmr spectra; only the carbodiimide 8c was observed.A mechanistic rationalization is presented in Scheme 1.
