Synthesis of E,E ‐diene hydroperoxides via photoisomerization of protected hydroperoxides | Zendy

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

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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.

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