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Title: Reactions of trichloroacetyl isothiocyanate with organic azides
Authors: Labbe, G ×
Bosman, J
Toppet, Suzanne #
Issue Date: Jan-1992
Publisher: Hetero corporation
Series Title: Journal of heterocyclic chemistry vol:29 issue:1 pages:17-23
Abstract: 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 C-13 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 H-1 nmr spectra; only the carbodiimide Bc was observed. A mechanistic rationalization is presented in Scheme 1.
ISSN: 0022-152X
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Molecular Design and Synthesis
× corresponding author
# (joint) last author

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