Abstract
The photosensitized oxidation of cholest-4-en-3β-ol in which singlet molecular oxygen is implicated yielded cholest-4-en-3-one and the isomeric epoxides 4α,5-epoxy-5α-cholestan-3-one and 4β,5-epoxy-5β-cholestan-3-one, the epoxides being formed in the ratio 3 : 1. Oxidation of cholest-4-en-3-one by alkaline hydrogen peroxide likewise yielded the isomeric 4,5-epoxides but in the ratio 1 : 7.4. Attempted use of cholest-4-en-3β-ol to intercept singlet molecular oxygen putatively generated in the disproportionation of hydrogen peroxide gave a very complex product mixture of over 50 components from which only cholest-4-en-3-one could be identified. However, neither isomeric 4,5-epoxycholestan-3-one was detected among the products. These data establish that it is unwarranted to infer the action of single molecular oxygen in systems containing cholest-4-en-3β-ol merely by product analysis where the product 4α,5-epoxy-5α-cholestan-3-one is formed.
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