Diethyl chlorophosphite: A versatile reagent

Zhou Jie; Vebumani Rammoorty; Bilha Fischer

doi:10.1021/jo0106851

Diethyl chlorophosphite: A versatile reagent

Zhou Jie
, Vebumani Rammoorty
, Bilha Fischer

Department of Chemistry

Bar-Ilan University

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

34 Scopus citations

Abstract

Diethyl chlorophosphite (DECP) was previously described as a reducing agent for nitro compounds to the corresponding amines (Fischer, B.; Sheihet, L. J. Org. Chem. 1998, 63, 393). Here, the utility of this reagent was extended to chemical conversions of other oxygenated functional groups. In this paper we report on the scope of the reaction of DECP with N-oxides, epoxides, sulfones, sulfoxides, hydroxylamines, ketoximes, and aldoximes. The chemoselectivity of DECP is described, and conditions for a stepwise multiple conversion of functional groups on the same molecule with this reagent are provided.

Original language	English
Pages (from-to)	711-719
Number of pages	9
Journal	Journal of Organic Chemistry
Volume	67
Issue number	3
DOIs	https://doi.org/10.1021/jo0106851
State	Published - 8 Feb 2002

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AB - Diethyl chlorophosphite (DECP) was previously described as a reducing agent for nitro compounds to the corresponding amines (Fischer, B.; Sheihet, L. J. Org. Chem. 1998, 63, 393). Here, the utility of this reagent was extended to chemical conversions of other oxygenated functional groups. In this paper we report on the scope of the reaction of DECP with N-oxides, epoxides, sulfones, sulfoxides, hydroxylamines, ketoximes, and aldoximes. The chemoselectivity of DECP is described, and conditions for a stepwise multiple conversion of functional groups on the same molecule with this reagent are provided.

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Diethyl chlorophosphite: A versatile reagent

Abstract

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