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The mechanism of the photooxidation of 1-(9-phenanthryl)-4-phenyl-1-buten-3-yne

✍ Scribed by R. J. F. M. van Arendonk; W. H. Laarhoven

Publisher
Elsevier Science
Year
2010
Tongue
English
Weight
527 KB
Volume
100
Category
Article
ISSN
0165-0513

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✦ Synopsis

Abstract

Irradiation of 1‐(9‐phenanthryl)‐4‐phenylbutenyne (1) in aprotic solvents containing oxygen gives two products, namely a photocyclization product, 1‐phenyltriphenylene 3, as is usually formed from diarylbutenynes, and a photooxidation product (2), derived from cyclopropapyrone. The formation of the latter product is rather specific to the butenyne 1.

Both products arise from singlet‐ excited butenyne, probably via the same cycloallene intermediate 4. Supposedly, this intermediate is converted by triplet oxygen into a 1,2‐dioxetane, having an exocyclic double bond, from which the oxidation product can be formed by ring opening and further rearrangements. The negligible photooxidation of other butenynes is ascribed to the much shorter lifetime of the corresponding cyclic allenes.

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