Research & Teaching Faculty

Default Header Image

An unexpected Paterno-Buchi reaction in the crystalline state

TitleAn unexpected Paterno-Buchi reaction in the crystalline state
Publication TypeJournal Article
Year of Publication2001
AuthorsKang, T, Scheffer, JR
JournalOrganic Letters
Volume3
Pagination3361-3364
Date PublishedOct
Type of ArticleArticle
ISBN Number1523-7060
KeywordsASYMMETRIC INDUCTION, ORGANIC-PHOTOCHEMISTRY, PHOTOCYCLOADDITION, SALTS, SOLID-STATE, YANG PHOTOCYCLIZATION REACTION
Abstract

[GRAPHICS] The solution and solid-state photochemistry of a series of aryl 1-phenylcyclopentyl ketones (1) was investigated. While typical Norrish type I products were formed in solution, irradiation of crystals of I afforded the novel oxetanes 3 and 4 regiospecifically. The formation of the oxetanes is believed to occur through Norrish type I cleavage and hydrogen abstraction, producing an alkene and an aldehyde, followed by a Paternb-BUchi reaction within the crystal lattice cage.

URL<Go to ISI>://000171708000034