Radical cyclization reactions of 4-bromo vinylogous-esters, vinylogous-amides and enones

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Chin-Kang Sha, Wei-Hong Tseng, Kuan-Tsau Huang, Kuan-Miao Liu, Herng-Yih Lin and San-Yan Chu


Abstract

Radicals generated from 4-bromo vinylogous-esters, vinylogous-amides and enones cyclize to a tethered acetylene side-chain preferentially at the γ-position; theoretical calculations of the spin density of the radicals and the relative stability of the radical intermediates are performed to rationalize the experimental observations.


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