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17.4.3.2.1.1.2 Variation 2: Electrocyclic Chemistry

DOI: 10.1055/sos-SD-017-01065

Schwan, A. L.Science of Synthesis, (200417712.

The reaction of sulfur dioxide with 2 equivalents of vinyl diazomethane is thought to afford a transient divinyl episulfone, which rapidly undergoes an electrocyclic ring opening to 4,5-dihydrothiepin 1,1-dioxide (25).[‌42‌] Radical bromination to give 26 followed by ­hydrogen bromide elimination offers an alternative route to thiepin 20 (Scheme 9). The method has not been generalized although the initial step also works with prop-1-enyl ­diazomethane.[‌42‌]

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