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Synthesis of E,E ‐diene hydroperoxides via photoisomerization of protected hydroperoxides
Author(s) -
Dussault P. H.,
Lee I. Q.,
Eary C. T.
Publication year - 1995
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/bf02536994
Subject(s) - photoisomerization , diene , lipidology , chemistry , isomerization , clinical chemistry , organic chemistry , photochemistry , catalysis , biochemistry , natural rubber
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.