ISSN:
0009-2940
Keywords:
Epoxidation
;
Dioxirane, dimethyl
;
Benzofurans, 2,3-dimethyl-
;
Benzofuran epoxides
;
Quinone methides
;
Methanol addition
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The synthesis of epoxides 2 by the reaction of the chloro- and methyl-substituted 2,3-dimethylbenzofurans 1 with dimethyl-dioxirane at low temperature is reported. These labile epoxides were spectroscopically characterized (1H and 13C NMR) at subambient temperatures. Epoxidation of benzofuran 1c affords a 31:69 mixture of epoxide 2c and quinone methide 3c, the latter presumably being produced by valence isomerization of the epoxide. On warming up above -10°C, the epoxides 2 suffer decomposition. Treatment of epoxide 21 with methanol yields the tautomeric mixture of adducts 4i and 4i′.
Additional Material:
2 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19921250136
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