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The photo-oxidation of hexamethylbenzene and pentamethylbenzene by singlet oxygen

✍ Scribed by C. J. M. van den Heuvel; A. Hofland; H. Steinberg; Th. J. de Boer

Publisher
Elsevier Science
Year
2010
Tongue
English
Weight
470 KB
Volume
99
Category
Article
ISSN
0165-0513

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✦ Synopsis

Abstract

In a two step reaction, hexamethylbenzene consumes two molecules of singlet oxygen to form epidioxy hydroperoxide 3. The first step involves a [4 + 2]‐cycloaddition, which is followed by an ene‐reaction. The structure of the intermediary endoperoxide 2 has been established spectroscopically. Pentamethylbenzene reacts in the same way with singlet oxygen, albeit much more slowly. Two epidioxy hydroperoxides are formed in this case.

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