Abstract
AbstractProtodemetallation of (Z)‐1‐aryl‐2‐germyl‐1‐stannylethenes using hydrochloric acid in the presence of tetraethylammonium chloride (TEACl) proceeds at 0 °C with retention of configuration to afford trans‐1‐aryl‐2‐germylethenes with high yields. In contrast, the reaction using hydroiodic acid in the presence of tetrabutylammonium iodide (TBAI) brings about a novel 1,2‐germyl migration accompanying the destannylation to form 1‐aryl‐1‐germylethenes. These 1,2‐germyl migration products result with especially high selectivity from adducts bearing a substituent at the ortho‐ or para‐position on the aromatic ring in the adduct. However, the germyl(stannyl)ethenes bearing a substituent at the meta position on the ring produce a regioisomeric mixture of a trans‐germylethene and a 1‐aryl‐1‐germylethene. Copyright © 2005 John Wiley & Sons, Ltd.
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