Photochemical Cycloaddition of Phenanthrene-Fused Lactones to (E)-Anethole. Structural Effects and Dual Collapse Processes of an Exciplex Leading to Cycloadducts

On irradiation with (E)-anethole in benzene 10-hydroxymethyl-9-phenanthrenecarboxylic acid lactone (s-trans lactone, STL) gave an intermolecular [2+2] cycloadduct, a cyclobutane derivative, while 8-hydroxymethyl-9-phenanthrenecarboxylic acid lactone (s-cis lactone, SCL) afforded a cyclobutane deriva...

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Published inBulletin of the Chemical Society of Japan Vol. 66; no. 1; pp. 287 - 293
Main Authors Itoh, Hiroki, Maruyama, Syuji, Fujii, Yoshiharu, Senda, Yasuhisa, Sakuragi, Hirochika, Tokumaru, Katsumi
Format Journal Article
LanguageEnglish
Published Tokyo The Chemical Society of Japan 01.01.1993
Chemical Society of Japan
Subjects
Chemistry
Exact sciences and technology
General and physical chemistry
Photochemistry
Physical chemistry of induced reactions (with radiations, particles and ultrasonics)
Exciplex
Cycloaddition
Near ultraviolet radiation
Frontier orbital
Lactone
Aromatic compound
Tetracyclic compound
Photochemical reaction
Oxygen heterocycle
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Summary:On irradiation with (E)-anethole in benzene 10-hydroxymethyl-9-phenanthrenecarboxylic acid lactone (s-trans lactone, STL) gave an intermolecular [2+2] cycloadduct, a cyclobutane derivative, while 8-hydroxymethyl-9-phenanthrenecarboxylic acid lactone (s-cis lactone, SCL) afforded a cyclobutane derivative and an olefinic product derived from an oxetane precursor, the carbonyl adduct. The formation of cycloadducts of highly different structures in SCL was ascribed to competitive collapse of the involved exciplex to the products. The features of intermolecular cycloaddition of the phenanthrene derivatives are discussed on the basis of results obtained from molecular orbital calculations.
ISSN:0009-2673
1348-0634
DOI:10.1246/bcsj.66.287