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The Effect of Solvent on Competing Hydroperoxide and Dioxetane Formation on Photo-Sensitized Oxygenation of Olefins

✍ Scribed by Charles W. Jefford; Shigeo Kohmoto

Publisher
John Wiley and Sons
Year
1982
Tongue
German
Weight
213 KB
Volume
65
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The rates of the competitive photo‐sensitized oxygenation of 2‐isobutylideneadamantane (1) and 2‐propylidene‐adamantane (2) with 1, 1‐di‐t‐butyl‐2‐methoxyethane (3) in various solvents were determined. The rates for 1 and 2 were independent of solvent, whereas that for 3 varied markedly with solvent polarity. Compounds 1 and 2 gave only hydroperoxides while 3 gave dioxetane. These results are interpreted in terms of two competing processes involving little and much charge separation leading to hydroperoxide and dioxetane, respectively.

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