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Benzophenone sensitized rearrangement of furylidentetralones

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
46
Issue
23
Identifiers
DOI: 10.1016/s0040-4020(01)90080-8

Abstract

Abstract Benzophenone sensitized rearrangement of furylidentetralones into dihydronaphthofuran derivatives was described. All the obtained compounds ( 6a , b , c , d , f ) showed a trans -double bond in α-position on the furan ring. Only using the methoxy derivative 5e the formation of a little amount of cis -isomer was observed. Furylidenacetone, furylidenacetophenone, and furylidenindanone did not show this reaction in agreement with the hypothesis that the observed intramolecular rearrangement is strictly related to the presence of tetralone moiety. An explanation of this behaviour on the basis of steric hindrance to conjugation in the starting materials was reported.

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