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Enhanced regioselectivity of Yang photocyclization in the crystalline state

TitleEnhanced regioselectivity of Yang photocyclization in the crystalline state
Publication TypeJournal Article
Year of Publication2002
AuthorsVishnumurthy, K, Cheung, E, Scheffer, JR, Scott, C
JournalOrganic Letters
Volume4
Pagination1071-1074
Date PublishedApr
Type of ArticleArticle
ISBN Number1523-7060
KeywordsABSTRACTION, GAMMA, GEOMETRIC REQUIREMENTS, II REACTION, PHOTOCHEMISTRY, SOLID-STATE
Abstract

[GRAPHICS] In contrast to the solution state, where Yang photocyclization of ketones of general structure 1 leads to equal amounts of cyclobutanols 2 and 3 (by abstraction of H-A and H-B, respectively), irradiation in the crystalline state is much more regioselective, favoring either 2 or 3 depending on the nature of the substituent X. X-ray crystallography and molecular mechanics calculations reveal the source of this remarkable solid-state regioselectivity.
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