Journal of Organic Chemistry p. 3053 - 3058 (1983)
Update date:2022-08-03
Topics:
Shimizu, Tomio
Hayashi, Yoshiyuki
Teramura, Kazuhiro
3,4-Bis(ethoxycarbonyl)-1,2,5-oxadiazole 2-oxide (1) has been shown to react with several olefins in a molar ratio of 1:2, giving 5-(ethoxycarbonyl)-1-aza-2,8-dioxabicyclo<3.3.0>octanes (2).Evidence is presented that these products arise from 1,3-dipolar cycloaddition, elimination of ethyl cyanoformate from the initial cycloadducts, and 1,3-dipolar cycloaddition of the resulting isoxazoline N-oxides with another mole of olefin.
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