Carbon–carbon bond formation by radical addition–fragmentation reactions of O-alkylated enols

…, BP Roberts, DA Tocher, SA Barnett

Index: Cai, Yudong; Roberts, Brian P.; Tocher, Derek A.; Barnett, Sarah A. Organic and Biomolecular Chemistry, 2004 , vol. 2, # 17 p. 2517 - 2529

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Citation Number: 19

Abstract

α-tert-Butoxystyrene [H2CC (OBut) Ph] reacts with α-bromocarbonyl or α-bromosulfonyl compounds [R1R2C (Br) EWG; EWG=–C (O) X or–S (O2) X] to bring about replacement of the bromine atom by the phenacyl group and give R1R2C (EWG) CH2C (O) Ph. These reactions take place in refluxing benzene or cyclohexane with dilauroyl peroxide or azobis (isobutyronitrile) as initiator and proceed by a radical-chain mechanism that involves ...

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