Bromination of Silatranyl-, Germatranyl-, Silyl-, and Germyl-phenylacetylenes

Abstract

Reactions of element-substituted alkynes R3MC≡CPh (R 3M = Me3Si, Et3Si, Ph3Si, Et 3Ge, n-Bu3Sn, N(CH2CH2O) 3Si, N(CH2CH2O)3Ge, N(CH 2CHMeO)3Ge, and N(CH2CH2O) 2(CH2CHPhO)Ge) with bromine, tetra-n-butylammonium tribromide (TBAT), and N-bromosuccinimide (NBS)/DMSO were investigated. The Z,E-ratio of isomeric dibromoalkenes formed in bromination reaction with Br 2 and TBAT are discussed. The crystal structures of N(CH 2CH2O)3SiC=CPh and N(CH2CHMeO) 3GeX (X=C≡ CPh, C(Br)=C(Br)Ph, C(Br2)C(O)Ph), and Ph3SiC-(Br)-C(Br)Ph are reported. © 2003 Wiley Periodicals, Inc.