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A Comparison of Intrazeolite and Solution Singlet Oxygen Ene Reactions of Allylic Alcohols
Author(s) -
Clennan Edward L.,
Zhang Dong,
Singleton Jamie
Publication year - 2006
Publication title -
photochemistry and photobiology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.818
H-Index - 131
eISSN - 1751-1097
pISSN - 0031-8655
DOI - 10.1562/2006-01-09-ra-768
Subject(s) - allylic rearrangement , chemistry , singlet oxygen , ene reaction , pyridine , photochemistry , decomposition , brønsted–lowry acid–base theory , organic chemistry , catalysis , oxygen , medicinal chemistry
The singlet oxygen ene reactions of four allylic alcohols and for comparison an allylic ether have been examined both in solution and in zeolite Y. Brønsted acid sites in the zeolite were shown to induce decomposition of several of the allylic alcohols. Treatment of the zeolites with pyridine removed these acid sites and allowed intrazeolite reactions of the allylic alcohols without interference from decomposition. Control reactions with an allylic alcohol that is inert to decomposition provided evidence that the presence of pyridine in the zeolite labyrinth does not influence the product composition.