Endoperoxides from conjugated dienes

Disubstituted peroxides are cleaved reductively by the same reagents as are used for hydroperoxides. The usual products are alcohols derived from the two substituents, but considerable selectivity is possible with some substrates. This is illustrated by the reduction of cyclic endoperoxides of the general formula (50) these compounds are available from the cycloaddition of singlet oxygen to cyclic conjugated dienes. The reduction of such compounds provides a good method of synthesis of cis-1,4-diols, which can be formed with retention of the double bond or with reduction of it (Scheme 29). It is also possible to prepare unsaturated epoxides by reduction with triphenylphosphine or other phosphorus(III) reagents. 

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