American Chemical Society
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Functionalization of Monofluoroallene and the Synthesis of Aryl-Substituted Conjugated Fluorodienes

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journal contribution
posted on 2002-06-13, 00:00 authored by Yunfeng Lan, Gerald B. Hammond
4-Fluoroallenol 3a, prepared from 1, cyclized easily to 4 but preserved its fluoroallenyl integrity under oxidation and SN2 displacement to yield aldehyde, amine, mesylate, and halide 6. Allylic isomerization yielded 2-halo-1-fluoro-1,3-butadiene 7, which underwent a Suzuki coupling to give aryl-substituted conjugated diene 8.