Thermal Reaction of 4-(p-Aminopheny1)-1-sulfonyl-1,2,3-triazoles Furnishing Benzoyl Cyanides through N-Sulfinyl Imine Intermediates

A thermal reaction of 4-(p-aminophenyl)-1-sulfonyl-1,2,3-triazoles forming benzoyl cyanides is reported. A carbene species thermally generated from the triazole by denitrogenation undergoes intramolecular oxygen migration from sulfur to carbon, giving an N-sulfinyl benzoylimine intermediate. The sub...

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Bibliographic Details
Published inChemistry letters Vol. 44; no. 7; pp. 967 - 969
Main Authors Miura, Tomoya, Zhao, Qiang, Funakoshi, Yuuta, Murakami, Masahiro
Format Journal Article
LanguageEnglish
Published TOKYO Chemical Soc Japan 05.07.2015
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
CATALYZED 3+2 CYCLOADDITION
REARRANGEMENT
DONOR/ACCEPTOR CARBENES
SULFONYL AZIDES
NITRILES
ONE-POT
1,2,3-TRIAZOLES
TERMINAL ALKYNES
TRANSANNULATION
H INSERTIONS
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Summary:A thermal reaction of 4-(p-aminophenyl)-1-sulfonyl-1,2,3-triazoles forming benzoyl cyanides is reported. A carbene species thermally generated from the triazole by denitrogenation undergoes intramolecular oxygen migration from sulfur to carbon, giving an N-sulfinyl benzoylimine intermediate. The subsequent Cope-type elimination of the sulfinyl group gives rise to cyano functionality.
ISSN:0366-7022
1348-0715
DOI:10.1246/cl.150320