Formation and reactivity of 1,3-benzodioxol-2-yl, 1,3-benzodioxan-2-yl, and related radicals. A search for an aromatic analog of the radical acetoxy rearrangement (Surzur–Tanner reaction)

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Abstract
Reaction of the 1,3-dioxole, 9, the 1,3-dioxan, 18, and the 1,3-dioxepin, 29, with tert-butoxy radicals gave evidence in each case for formation of the corresponding 1,1-dioxyethyl radicals. No conclusive evidence for formation of any of these radicals by cyclization of acetoxyaryl radicals could be obtained. Several of the 1,1-dioxyethyl radicals reacted by rearrangement.

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