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26.3.4.1.3.1 Variation 1: Addition of Dialkoxycarbenes to Ketones

DOI: 10.1055/sos-SD-026-00451

Salaün, J.Science of Synthesis, (200526620.

Cyclopropanone acetals 82 are obtained by addition of dialkoxycarbenes 81 to alkenes 80 (Scheme 30). The dialkoxycarbenes 81 can be generated either by thermolysis of dialkoxy­bicyclo[2.2.1]heptadiene derivatives,[‌87‌] by photolysis or thermolysis of 3,3-dialkoxydi­azirines,[‌88‌‌90‌] or by thermolysis of dialkoxyoxadiazoles.[‌91‌‌94‌] This method provides the dimethoxymethanofullerene 85 in 69% yield by thermolysis of dimethoxyoxadiazole 84[‌91‌,‌92‌] and treatment with buckminsterfullerene 83 (C60), as shown in Scheme 30.[‌93‌]

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