Bromination of silatranyl‐, germatranyl‐, silyl‐, and germyl‐phenylacetylenes

Abstract

Abstract Reactions of element‐substituted alkynes R 3 MCCPh (R 3 M = Me 3 Si, Et 3 Si, Ph 3 Si, Et 3 Ge, n‐Bu 3 Sn, N(CH 2 CH 2 O) 3 Si, N(CH 2 CH 2 O) 3 Ge, N(CH 2 ‐CHMeO) 3 Ge, and N(CH 2 CH 2 O) 2 (CH 2 CHPhO)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 2 CH 2 O) 3 SiCCPh and N(CH 2 CHMeO) 3 GeX (X = C CPh, C(Br)C(Br)Ph, C(Br 2 )C(O)Ph), and Ph 3 SiC(Br)C(Br)Ph are reported. © 2003 Wiley Periodicals, Inc. 15:43–56, 2004; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/.hc10211