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  3. THE NOVEL SOLID-STATE AND SOLUTION PHASE PHOTOCHEMISTRY OF DIMETHYL 9-CHLOROMETHYL-9,10-DIHYDRO-9,10-ETHENOANTHRACENE-11,12-DICARBOXYLATE

THE NOVEL SOLID-STATE AND SOLUTION PHASE PHOTOCHEMISTRY OF DIMETHYL 9-CHLOROMETHYL-9,10-DIHYDRO-9,10-ETHENOANTHRACENE-11,12-DICARBOXYLATE

TitleTHE NOVEL SOLID-STATE AND SOLUTION PHASE PHOTOCHEMISTRY OF DIMETHYL 9-CHLOROMETHYL-9,10-DIHYDRO-9,10-ETHENOANTHRACENE-11,12-DICARBOXYLATE
Publication TypeJournal Article
Year of Publication1991
AuthorsChen, JX, Pokkuluri, PR, Scheffer, JR, Trotter, J
JournalJournal of Photochemistry and Photobiology a-Chemistry
Volume57
Pagination21-26
Date PublishedApr
Type of ArticleArticle
ISBN Number1010-6030
KeywordsMETHANE
Abstract

Although the triplet excited state behavior of dimethyl 9-chloromethyl-9,10-dihydro-9,10-ethenoanthracene-11,12-dicarboxylate (5) is normal, di-pi-methane photorearrangement to a 4:1 mixture of regioisomers 6 and 7, its singlet excited state reactivity is unusual and involves the formation of the novel photoproducts 8 and 9. The mechanism by which these products are formed is thought to involve photorearrangement to the 1,4-biradical 10 followed by a non-concerted chlorine atom migration. Photoproducts 8 and 9 are more prevalent in solid state photolyses compared with those carried out in solution, a result that may be related to a favorable (4.28 angstrom) intermolecular C...Cl contact in crystals of 5.
URL<Go to ISI>://A1991FJ78100004