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THE NOVEL PHOTOCHEMICAL BEHAVIOR OF TRIPTYCENE-1,4-QUINONE

TitleTHE NOVEL PHOTOCHEMICAL BEHAVIOR OF TRIPTYCENE-1,4-QUINONE
Publication TypeJournal Article
Year of Publication1995
AuthorsFu, TY, Gamlin, JN, Olovsson, G, Scheffer, JR, Trotter, J, Young, DT
JournalTetrahedron Letters
Volume36
Pagination2025-2028
Date PublishedMar
Type of ArticleArticle
ISBN Number0040-4039
Keywords10-DIHYDRO-9, 10-ORTHO-BENZENOANTHRACENE-1, 4-DIONES, 9, ABSTRACTION, DERIVATIVES, INTRAMOLECULAR CHARGE-TRANSFER, TRANSITION
Abstract

Triptycene-1,4-quinone (1) reacts photochemically in solution to give different products depending on the solvent employed and on the presence or absence of oxygen. The structures of the photoproducts have been elucidated by spectroscopic methods, independent synthesis and single crystal X-ray diffractometry, and possible mechanistic pathways leading to their formation are presented and discussed. Unexpectedly, quinone 1 was found to be photochemically inert in the crystalline state. The X-ray crystal structure of 1 reveals the probable reason for this behavior.

URL<Go to ISI>://A1995QP02000014