Selective oxidation of primary-secondary diols with methyl hypochlorite in acid buffered medium

P.S.G. Tassignon; D. de Wit; T.C. de Rijk; L.F. de Buyck

doi:10.1016/0040-4020(95)00747-V

Selective oxidation of primary-secondary diols with methyl hypochlorite in acid buffered medium

P.S.G. Tassignon, D. de Wit, T.C. de Rijk, L.F. de Buyck

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

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Abstract

A convenient, low cost method was developed for the selective oxidation of secondary alcohols, leaving primary alcohol functions intact. Methyl hypochlorite, generated from chlorine or trichloroisocyanuric acid in methanol, is used as a 'positive chlorine' reagent in the presence of an appropriate buffer which is acidic enough to warrant good transfer of 'positive chlorine'. 1,9(R)-octadecanediol was converted to 1-hydroxy-9-octadecanone with 98% selectivity.

Original language	English
Pages (from-to)	11863-11872
Journal	Tetrahedron
Volume	51
Issue number	43
DOIs	https://doi.org/10.1016/0040-4020(95)00747-V
Publication status	Published - 1995

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title = "Selective oxidation of primary-secondary diols with methyl hypochlorite in acid buffered medium",

abstract = "A convenient, low cost method was developed for the selective oxidation of secondary alcohols, leaving primary alcohol functions intact. Methyl hypochlorite, generated from chlorine or trichloroisocyanuric acid in methanol, is used as a 'positive chlorine' reagent in the presence of an appropriate buffer which is acidic enough to warrant good transfer of 'positive chlorine'. 1,9(R)-octadecanediol was converted to 1-hydroxy-9-octadecanone with 98% selectivity.",

author = "P.S.G. Tassignon and {de Wit}, D. and {de Rijk}, T.C. and {de Buyck}, L.F.",

year = "1995",

doi = "10.1016/0040-4020(95)00747-V",

language = "English",

volume = "51",

pages = "11863--11872",

journal = "Tetrahedron",

issn = "0040-4020",

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T1 - Selective oxidation of primary-secondary diols with methyl hypochlorite in acid buffered medium

AU - Tassignon, P.S.G.

AU - de Wit, D.

AU - de Rijk, T.C.

AU - de Buyck, L.F.

PY - 1995

Y1 - 1995

N2 - A convenient, low cost method was developed for the selective oxidation of secondary alcohols, leaving primary alcohol functions intact. Methyl hypochlorite, generated from chlorine or trichloroisocyanuric acid in methanol, is used as a 'positive chlorine' reagent in the presence of an appropriate buffer which is acidic enough to warrant good transfer of 'positive chlorine'. 1,9(R)-octadecanediol was converted to 1-hydroxy-9-octadecanone with 98% selectivity.

AB - A convenient, low cost method was developed for the selective oxidation of secondary alcohols, leaving primary alcohol functions intact. Methyl hypochlorite, generated from chlorine or trichloroisocyanuric acid in methanol, is used as a 'positive chlorine' reagent in the presence of an appropriate buffer which is acidic enough to warrant good transfer of 'positive chlorine'. 1,9(R)-octadecanediol was converted to 1-hydroxy-9-octadecanone with 98% selectivity.

U2 - 10.1016/0040-4020(95)00747-V

DO - 10.1016/0040-4020(95)00747-V

M3 - Article

VL - 51

SP - 11863

EP - 11872

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 43

ER -

Selective oxidation of primary-secondary diols with methyl hypochlorite in acid buffered medium

Abstract

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