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SELECTIVE SOLID-STATE PHOTOREARRANGEMENT THROUGH THE LESS STABLE OF 2 POSSIBLE BIRADICAL INTERMEDIATES

TitleSELECTIVE SOLID-STATE PHOTOREARRANGEMENT THROUGH THE LESS STABLE OF 2 POSSIBLE BIRADICAL INTERMEDIATES
Publication TypeJournal Article
Year of Publication1992
AuthorsPokkuluri, PR, Scheffer, JR, Trotter, J, Yap, M
JournalJournal of Organic Chemistry
Volume57
Pagination1486-1494
Date PublishedFeb
Type of ArticleArticle
ISBN Number0022-3263
KeywordsCRYSTALS, EXPLORATORY ORGANIC-PHOTOCHEMISTRY, HYDROGEN ABSTRACTION REACTIONS, POLAR SUBSTITUENTS, REARRANGEMENT
Abstract

The photochemistry of methyl 2-benzoyl-1,4-dihydro-1,4-ethenonaphthalene-3-carboxylate is completely medium-dependent. In solution, two primary di-pi-methane-type photoproducts are formed. Neither of these products is produced when the photolysis is carried out in the solid state; instead, three new photoproducts are formed. The results are interpreted as being due to reaction through 1,3-biradical intermediates, the more stable of which are preferred in solution whereas the less stable ones are formed in the solid state as a result of topochemical restrictions of molecular motion. X-ray crystallographic evidence in support of these ideas is presented and discussed.
URL<Go to ISI>://A1992HG74100030