[2,3]-wittig rearrangement initiated by 1,5-hydrogen atom transfer from ano-iodophenyl group on the alpha-carbon of allylic ethers by reduction withSmI2

Intramolecular 1,5-hydrogen atom transfer of an aryl radical generated by r eduction of an o-iodophenyl group on the allylic position of allyl ethers b y SmI2 regioselectively generates alpha-allyloxy carbanions, which undergo [2,3]-Wittig rearrangement to afford a substituted 4-phenyl-3-buten-1-ol. T he effect of HMPA concentration on distribution of the 1,5-hydrogen transfe r giving Wittig rearranged products and hydrogen abstraction giving reducti ve deiodination products is described.