Some further observations on the lewis-acid- catalysed oxygenation of ergosteryl acetate

Richard K. Haynes

doi:10.1071/CH9780121

Some further observations on the lewis-acid- catalysed oxygenation of ergosteryl acetate

Richard K. Haynes

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Abstract

Some qualitative observations on the catalytic activity of Lewis acids in converting ergosteryl acetate into its 5α, 8α peroxide are presented. The peroxide has an inhibiting effect on the reaction, which is ascribed to complex formation between it and the Lewis acid catalyst. This complex formation is used to explain the dual thermal and photochemical activity displayed by FeCl₃ and MoCl₅. A mixed oxygenation experiment with ergosteryl and lumisteryl acetates indicates that singlet oxygen is not an intermediate in this reaction. A model for the reaction, involving formation of a diene cation radical within a charge-transfer complex, is advanced.

Original language	English
Pages (from-to)	121-129
Number of pages	9
Journal	Australian Journal of Chemistry
Volume	31
Issue number	1
DOIs	https://doi.org/10.1071/CH9780121
Publication status	Published - 1978

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abstract = "Some qualitative observations on the catalytic activity of Lewis acids in converting ergosteryl acetate into its 5α, 8α peroxide are presented. The peroxide has an inhibiting effect on the reaction, which is ascribed to complex formation between it and the Lewis acid catalyst. This complex formation is used to explain the dual thermal and photochemical activity displayed by FeCl3 and MoCl5. A mixed oxygenation experiment with ergosteryl and lumisteryl acetates indicates that singlet oxygen is not an intermediate in this reaction. A model for the reaction, involving formation of a diene cation radical within a charge-transfer complex, is advanced.",

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N2 - Some qualitative observations on the catalytic activity of Lewis acids in converting ergosteryl acetate into its 5α, 8α peroxide are presented. The peroxide has an inhibiting effect on the reaction, which is ascribed to complex formation between it and the Lewis acid catalyst. This complex formation is used to explain the dual thermal and photochemical activity displayed by FeCl3 and MoCl5. A mixed oxygenation experiment with ergosteryl and lumisteryl acetates indicates that singlet oxygen is not an intermediate in this reaction. A model for the reaction, involving formation of a diene cation radical within a charge-transfer complex, is advanced.

AB - Some qualitative observations on the catalytic activity of Lewis acids in converting ergosteryl acetate into its 5α, 8α peroxide are presented. The peroxide has an inhibiting effect on the reaction, which is ascribed to complex formation between it and the Lewis acid catalyst. This complex formation is used to explain the dual thermal and photochemical activity displayed by FeCl3 and MoCl5. A mixed oxygenation experiment with ergosteryl and lumisteryl acetates indicates that singlet oxygen is not an intermediate in this reaction. A model for the reaction, involving formation of a diene cation radical within a charge-transfer complex, is advanced.

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Some further observations on the lewis-acid- catalysed oxygenation of ergosteryl acetate

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