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Photochemistry of triptycene-1,4-quinone

TitlePhotochemistry of triptycene-1,4-quinone
Publication TypeJournal Article
Year of Publication1998
AuthorsFu, TY, Gamlin, JN, Olovsson, G, Scheffer, JR, Trotter, J, Young, DT
JournalActa Crystallographica Section C-Crystal Structure Communications
Volume54
Pagination116-119
Date PublishedJan
Type of ArticleArticle
ISBN Number0108-2701
Abstract

Photolysis of 9,10-dihydro-9,10[1’,2’]benzenoanthracene-1’,4’-quinone C20H12O2, in oxygenated acetone gives the novel photoproduct 9,10-dihydro-9,10-ethanoanthracen-11-one-12-spiro-2’-cyclopent-4’-ene-1’ ,3’-dione, C20H12O3. The reactant quinone molecule has ideal mm symmetry and lies on a crystallographic mirror plane in Pnma; the photoproduct molecule has ideal m symmetry, which is not utilized in packing in Pna2(1). This product is formed only in the presence of oxygen and a mechanism for its formation is proposed. Unreactivity in attempted solid-state photolysis can be rationalized in terms of crystal packing.

URL<Go to ISI>://000071962800053