Synthesis of E,E-diene hydroperoxides via photoisomerization of protected hydroperoxides

P. H. Dussault; I. Q. Lee; C. T. Eary

doi:10.1007/BF02536994

Synthesis of E,E-diene hydroperoxides via photoisomerization of protected hydroperoxides

P. H. Dussault, I. Q. Lee, C. T. Eary

Chemistry

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

Abstract

A general approach to E,E-diene hydroperoxides is described based upon photoisomerization of readily available Z,E-diene monoperoxyketals. Protection of a Z,E-diene hydroperoxide as the 2-methoxypropyl peroxyketal is followed by iodine-mediated photoisomerization to produce a mixture enriched in the E,E isomer. After chromatographic purification, deprotection of the peroxyketal with mild acid furnishes the E,E-diene hydroperoxide.

Original language	English (US)
Pages (from-to)	591-594
Number of pages	4
Journal	Lipids
Volume	30
Issue number	7
DOIs	https://doi.org/10.1007/BF02536994
State	Published - Jul 1995

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Cell Biology

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10.1007/BF02536994

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title = "Synthesis of E,E-diene hydroperoxides via photoisomerization of protected hydroperoxides",

abstract = "A general approach to E,E-diene hydroperoxides is described based upon photoisomerization of readily available Z,E-diene monoperoxyketals. Protection of a Z,E-diene hydroperoxide as the 2-methoxypropyl peroxyketal is followed by iodine-mediated photoisomerization to produce a mixture enriched in the E,E isomer. After chromatographic purification, deprotection of the peroxyketal with mild acid furnishes the E,E-diene hydroperoxide.",

author = "Dussault, {P. H.} and Lee, {I. Q.} and Eary, {C. T.}",

year = "1995",

month = jul,

doi = "10.1007/BF02536994",

language = "English (US)",

volume = "30",

pages = "591--594",

journal = "Lipids",

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T1 - Synthesis of E,E-diene hydroperoxides via photoisomerization of protected hydroperoxides

AU - Dussault, P. H.

AU - Lee, I. Q.

AU - Eary, C. T.

PY - 1995/7

Y1 - 1995/7

N2 - A general approach to E,E-diene hydroperoxides is described based upon photoisomerization of readily available Z,E-diene monoperoxyketals. Protection of a Z,E-diene hydroperoxide as the 2-methoxypropyl peroxyketal is followed by iodine-mediated photoisomerization to produce a mixture enriched in the E,E isomer. After chromatographic purification, deprotection of the peroxyketal with mild acid furnishes the E,E-diene hydroperoxide.

AB - A general approach to E,E-diene hydroperoxides is described based upon photoisomerization of readily available Z,E-diene monoperoxyketals. Protection of a Z,E-diene hydroperoxide as the 2-methoxypropyl peroxyketal is followed by iodine-mediated photoisomerization to produce a mixture enriched in the E,E isomer. After chromatographic purification, deprotection of the peroxyketal with mild acid furnishes the E,E-diene hydroperoxide.

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IS - 7

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Synthesis of E,E-diene hydroperoxides via photoisomerization of protected hydroperoxides

Abstract

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