Synthesis of E,E-diene hydroperoxides via photoisomerization of protected hydroperoxides.
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.
Dussault
P H
PH
Department of Chemistry, University of Nebraska-Lincoln 68588-0304, USA.
Lee
I Q
IQ
Eary
C T
CT
D002851:Chromatography, High Pressure Liquid; D006861:Hydrogen Peroxide / Q000737:chemistry* / Q000378:metabolism*; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010782:Photolysis; D013237:Stereoisomerism
D006861:Hydrogen Peroxide