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Abstract (−)‐cis‐Pulegol (1) and (+)‐pulegone (2) readily add one mole of oxygen on dyesensitized photo‐oxygenation in solution, forming almost exclusively allyl hydroperoxides. The product distributions and structures of the peroxides (B–E) have been derived from analysis of their reduction products. Compound 1 yielded only the diols 4, 5 and 6, besides the epoxyketones 7 and 8 formed directly from the hydroperoxide C (proportions of 4–8, ∼21:56:13:4:6), while 2 gave the keto‐alcohols 9,10 and 11 (∼80:6:14) as the sole products. The course of addition of O2(1Δg) on 1 and 2 was found in all cases to be independent of solvent and photosensitizer.
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SCHULTE‐ELTE et al. (1971) studied this question.
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