Tetrahedron p. 2069 - 2080 (1985)
Update date:2022-08-03
Topics:
Griffin, Gary W.
Kirschenheuter, Gary P.
Vaz, Caetan
Umrigar, Pesi P.
Lankin, David C.
Christensen, Siegfried
A series of Me substituted 1,2-diphenylcyclobutenes was subjected to dye-sensitized photooxidation in the presence of methylene blue.In the case of the 3,3-dimethyl-, 3,3,4-trimethyl- and 3,3,4,4-tetramethyl-1,2-diphenylcyclobutenes, the sensitized oxidations are accompanied by ring-contraction with concomitant ortho hydroxylation of one aromatic nucleus.When electron transfer induced photooxidation techniques utilizing 9,10-dicyanoanthracene (DCA) as a sensitizer are employed with the series of Me substituted diphenylcyclobutenes, the reactions take a markedly different course and a broad spectrum of oxidation products are obtained including, most notably, ozonides of the cyclobutenes.The mechanisms of these conversions are addressed and the significance of the results discussed.
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