Issue 0, 1972
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Studies on conformation and reactivity. Part XI. Photochemical oxidation, ozonolysis, and rearrangement of 5′,6′-dihydrocholesta-3,5-dieno[3,4-b][1,4]oxathiin

Akio Miyake  and  Munemitsu Tomoeda  

Abstract

The 3,4-double bond of the delocalized p-electron system in 5′,6′-dihydrocholesta-3,5-dieno[3,4-b][1,4]oxathiin (I) shows a specific reactivity towards photo-oxidation and ozonolysis. Photo-oxidation of the oxathiin (I) gives 3,4-secocholest-5-eno[3,4-b][1,4]oxathian-3,4-dione (IV) under anhydrous conditions, but when water is present, in addition to (IV), 6β-hydroxy-4-(2-hydroxyethylthio)cholest-4-en-3-one (V) is produced. Ozonolysis of the oxathiin (I) affords similar results, giving the seco-dione (IV), 6β-ethoxy-(XVII) and 6β-acetoxy-(XXII) 4-(2-hydroxyethylthio)cholest-4-en-3-one, and 6β-ethoxy-(XIX) and 6β-acetoxy-(XXI) 3α-hydroxycholest-4-eno[3,4-b][1,4]oxathian 4′-oxide [derived from (XVII) and (XXII), respectively], depending on the conditions. The dehydrated analogue of the enone (V), 4-(2-hydroxyethylthio)cholesta-4,6-dien-3-one (XVI), is also isolated after ozonolysis.

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Article information

DOI
https://doi.org/10.1039/P19720000663
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1972, 663-671

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Studies on conformation and reactivity. Part XI. Photochemical oxidation, ozonolysis, and rearrangement of 5′,6′-dihydrocholesta-3,5-dieno[3,4-b][1,4]oxathiin

A. Miyake and M. Tomoeda, J. Chem. Soc., Perkin Trans. 1, 1972, 663 DOI: 10.1039/P19720000663

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