136795-98-7Relevant articles and documents
Preparation of 2H-Benzoxetes by Photoinduced Cycloaddition of Quinone Methides, Accessible by Dimethyldioxirane (DMD) Oxidation of 2,3-Dimethylbenzofurans
Adam, Waldemar,Sauter, Markus,Zuenkler, Corinna
, p. 1115 - 1118 (2007/10/02)
Irradiation (λ > 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 cycloaddition.T
Epoxidation of 2,3-Dimethylbenzofurans by Dimethyldioxirane
Adam, Waldemar,Bialas, Joachim,Hadjiarapoglou, Lazaros,Sauter, Markus
, p. 231 - 234 (2007/10/02)
The synthesis of epoxides 2 by the reaction of the chloro- and methyl-substituted 2,3-dimethylbenzofuranes 1 with dimethyldioxirane 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 deg C, the epoxides 2 suffer decomposition.Treatment of epoxide 2i with methanol yields the tautomeric mixture ofadducts 4i and 4i'.Key Words: Epoxidation / Dioxirane, dimethyl / Benzofurans, 2,3-dimethyl- / Benzofuran epoxides / Quinone methides / Methanol addition