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Concerning an unique intermediate in the formation of hydroperoxides and dioxetanes from monoolefins and singlet oxygen

✍ Scribed by G. Rousseau; A. Lechevallier; F. Huet; J.M. Conia

Publisher
Elsevier Science
Year
1978
Tongue
French
Weight
269 KB
Volume
19
Category
Article
ISSN
0040-4039

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✦ Synopsis

We recently described the regioselective addition of singlet oxygen ('02) to various cyclopropylethylenes and reported easy cyclopropyl hydrogen abstractions (Ia> ;

moreover with methoxy-substituted olefins we found a stereoselective control of the methoxy group which leads to a strong preference for H-abstraction cis to that group (lb-'). -

'OMe

Scheme 2

πŸ“œ SIMILAR VOLUMES

The formation of a peracetal and trioxan
The formation of a peracetal and trioxane from an enol ether with copper(II) triflate and oxygen: Unexpected oxygenation of aldol intermediates
✍ Simone C. Vonwiller; Jacqueline A. Warner; Simon T. Mann; Richard K. Haynes πŸ“‚ Article πŸ“… 1997 πŸ› Elsevier Science 🌐 French βš– 311 KB

The enol ether 7 undergoes rapid conversion into a 2:3 mixture of cis aldol9 and trans aldol 11 in the presence of copper(X) triflate (0.1 equiv) and water (1 equiv) in MeCN with no intermediate formation of the corresponding ketoaidehyde 12. In the presence of oxygen, slow oxygenation of the aldols