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Preparation of 2H-Benzoxetes by Photoinduced [2 + 2] Cycloaddition of Quinone Methides, Accessible by Dimethyldioxirane (DMD) Oxidation of 2,3-Dimethylbenzofurans

✍ Scribed by Adam, Waldemar ;Sauter, Markus ;Zünkler, Corinna

Publisher: Wiley (John Wiley & Sons)
Year: 1994
Tongue: English
Weight: 438 KB
Volume: 127
Category: Article
ISSN: 0009-2940
DOI: 10.1002/cber.19941270622

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✦ Synopsis

Epoxidation I Dioxirane, dimethyl-I Benzofurans, 2,3-dimethyl-I Benzofuran epoxides I Quinone methides I [2 + 21 Photocycloaddition I Benzoxetes I Hetero-Diels-Alder reaction

Irradiation (h > 366 nm) of the quinone methides 3, which were formed by valence isomerization of the methyl-, chloro-, and tert-butyl-substituted 2,3-dimethylbenzofuran epoxides 2, afforded the novel 2H-benzoxetes 4 by photochemical 12 + 21 cycloaddition. These strained and highly labile benzo-

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