Thermal reaction of 4-(p-aminophenyl)-1-sulfonyl-1,2,3-triazoles furnishing benzoyl cyanides through N-sulfinyl imine intermediates

Tomoya Miura; Qiang Zhao; Yuuta Funakoshi; Masahiro Murakami

doi:10.1246/cl.150320

Thermal reaction of 4-(p-aminophenyl)-1-sulfonyl-1,2,3-triazoles furnishing benzoyl cyanides through N-sulfinyl imine intermediates

Tomoya Miura, Qiang Zhao, Yuuta Funakoshi, Masahiro Murakami

Research output: Contribution to journal › Article › peer-review

8 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	967-969
Number of pages	3
Journal	Chemistry Letters
Volume	44
Issue number	7
DOIs	https://doi.org/10.1246/cl.150320
Publication status	Published - 2015
Externally published	Yes

ASJC Scopus subject areas

Chemistry(all)

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title = "Thermal reaction of 4-(p-aminophenyl)-1-sulfonyl-1,2,3-triazoles furnishing benzoyl cyanides through N-sulfinyl imine intermediates",

abstract = "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.",

author = "Tomoya Miura and Qiang Zhao and Yuuta Funakoshi and Masahiro Murakami",

note = "Publisher Copyright: {\textcopyright} 2015 The Chemical Society of Japan.",

year = "2015",

doi = "10.1246/cl.150320",

language = "English",

volume = "44",

pages = "967--969",

journal = "Chemistry Letters",

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publisher = "Chemical Society of Japan",

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T1 - Thermal reaction of 4-(p-aminophenyl)-1-sulfonyl-1,2,3-triazoles furnishing benzoyl cyanides through N-sulfinyl imine intermediates

AU - Miura, Tomoya

AU - Zhao, Qiang

AU - Funakoshi, Yuuta

AU - Murakami, Masahiro

PY - 2015

Y1 - 2015

N2 - 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.

AB - 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.

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U2 - 10.1246/cl.150320

DO - 10.1246/cl.150320

M3 - Article

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JO - Chemistry Letters

JF - Chemistry Letters

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IS - 7

ER -

Thermal reaction of 4-(p-aminophenyl)-1-sulfonyl-1,2,3-triazoles furnishing benzoyl cyanides through N-sulfinyl imine intermediates

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