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Thermal and Photochemical Rearrangement of 3-Substituted 2-Methylbenzofuran Epoxides and Their Valence-Isomeric Quinone Methides (1994)

Adam, Waldemar ; Käb, Günther ; Sauter, Markus

Weinheim : Wiley-Blackwell

Berichte der deutschen chemischen Gesellschaft 127 (1994), S. 433-436

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ISSN: 0009-2940

Keywords: Epoxidation ; Dioxirane, dimethyl- ; Benzofurans, 2-methyl- ; Benzofuran epoxides ; Quinone methides ; Photoisomerization ; Chromenes ; 3-Benzofuranones ; Chemistry ; Inorganic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: The dimethyldioxirane oxidation of the 3-substituted 2-methylbenzofurans 1 [1a: 3(E)-styryl, 1b: 3-acetoxy, 1c: 3-(tert-butyldimethylsilyloxy)] is reported. Only quinone methide 3a, none of the benzofuran epoxides 2a-c, could be detected by 1H- and 13C-NMR spectroscopy at low temperature (-30°C), which on photoisomerization led to chromene 7a. The benzofuran-3-ones 5b, c and the α-diketone 6c are presumably formed by thermal isomerization of the transient benzofuran epoxides 2b, c and quinone methide 3c.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/cber.19941270220

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