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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