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CRYSTAL-STRUCTURE CORRELATIONS IN THE PHOTOCHEMISTRY OF DIMETHYL 9,10-DIMETHYL-9,10-DIHYDRO-9,10-ETHENOANTHRACENE-11,12-DICARBOXYLATE

TitleCRYSTAL-STRUCTURE CORRELATIONS IN THE PHOTOCHEMISTRY OF DIMETHYL 9,10-DIMETHYL-9,10-DIHYDRO-9,10-ETHENOANTHRACENE-11,12-DICARBOXYLATE
Publication TypeJournal Article
Year of Publication1993
AuthorsPokkuluri, PR, Scheffer, JR, Trotter, J
JournalActa Crystallographica Section B-Structural Science
Volume49
Pagination107-116
Date PublishedFeb
Type of ArticleArticle
ISBN Number0108-7681
Keywords1, 2-MIGRATION, EXPLORATORY ORGANIC-PHOTOCHEMISTRY, PHOTOPRODUCTS, PI-METHANE REARRANGEMENT, SOLID-STATE PHOTOCHEMISTRY, SUBSTITUTED DIBENZOBARRELENE
Abstract

{The photochemistry of the title 9,10-dimethlydi-benzobarrelene-11,12-diester (1) in solution and in the solid state exhibits unique differences as a function of reaction medium. In acetone the normal di-pi-methane reaction leads to a semibull-valene derivative, dimethyl 4b,8b-dimethy-4b,8b,8c,-8d-tetrahydrodibenzo[a,f]cyclopropa[calpentalene -gc,8d-dicarboxylate (2), while in acetonitrile an additional cyclooctatetraene (COT) photoproduct, dimethyl 5,11-dimethyldibenzo[a,e]cyclooctene-6,12-dicarboxylate (3), is obtained. In the solid state a new pentalene, dimethyl 5, 10-dimethyl-5, 10-dihydro-indeno[2,1-a]indene-5,10-dicarboxylate (4), is formed as the major product. Crystal data for (1), (3) and (4): T = 294 K, Cu Kalpha

URL<Go to ISI>://A1993KM62900013