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Unusual photorearrangements of 9,10-disubstituted triptycene-1,4-quinone derivatives

TitleUnusual photorearrangements of 9,10-disubstituted triptycene-1,4-quinone derivatives
Publication TypeJournal Article
Year of Publication1996
AuthorsBorecka, B, Gamlin, JN, Gudmundsdottir, AD, Olovsson, G, Scheffer, JR, Trotter, J
JournalTetrahedron Letters
Volume37
Pagination2121-2124
Date PublishedMar
Type of ArticleArticle
ISBN Number0040-4039
Abstract

In contrast to triptycene-1,4-quinone (1a), which forms exclusively a di-pi-methane type product when irradiated in acetonitrile, photolysis of the 9,10-dialkyl-substituted triptycene quinones 1b and 1c leads to carbene-derived as well as hydrogen atom abstraction-derived photoproducts. Mechanistic schemes that are capable of rationalizing the results on stereoelectronic grounds are presented and discussed.
URL<Go to ISI>://A1996UC59000002