In the present letter, the first stereoselective radical 1,5 phenyl transfer from silicon to carbon is reported. Diphenyl(trimethylsilyl)silyl ethers, the corresponding germylated and stannylated derivatives, and also some silyl ethers derived from commercially available silicon protecting groups were tested in this ipso substitution reaction. Diastereoselectivities of up to 11:1 were obtained. (C) 1998 Elsevier Science Ltd. All rights reserved.