Copper Azide as a New Reagent for Syn-SN2 Displacement of 7-Sulfonyloxy α,β-Unsaturated Esters

Yoshinori Yamamoto; Naoki Asao

doi:10.1021/jo00306a001

Copper Azide as a New Reagent for Syn-S_N2 Displacement of 7-Sulfonyloxy α,β-Unsaturated Esters

Yoshinori Yamamoto, Naoki Asao

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

10 Citations (Scopus)

Abstract

The reaction of 7-sulfonyloxy a,β-unsaturated esters with NaN₃-CuX(or CuN₃) in polar aprotic solvents such as HMPA, DMSO, and DMF proceeds predominantly in a syn-S_N2 fashion, while the reaction with NaN₃ proceeds in an anti-S_N2 manner.

Original language	English
Pages (from-to)	5303-5304
Number of pages	2
Journal	Journal of Organic Chemistry
Volume	55
Issue number	19
DOIs	https://doi.org/10.1021/jo00306a001
Publication status	Published - 1990 Jan 1

ASJC Scopus subject areas

Organic Chemistry

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title = "Copper Azide as a New Reagent for Syn-SN2 Displacement of 7-Sulfonyloxy α,β-Unsaturated Esters",

abstract = "The reaction of 7-sulfonyloxy a,β-unsaturated esters with NaN3-CuX(or CuN3) in polar aprotic solvents such as HMPA, DMSO, and DMF proceeds predominantly in a syn-SN2 fashion, while the reaction with NaN3 proceeds in an anti-SN2 manner.",

author = "Yoshinori Yamamoto and Naoki Asao",

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AB - The reaction of 7-sulfonyloxy a,β-unsaturated esters with NaN3-CuX(or CuN3) in polar aprotic solvents such as HMPA, DMSO, and DMF proceeds predominantly in a syn-SN2 fashion, while the reaction with NaN3 proceeds in an anti-SN2 manner.

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