Protodemetallation 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.
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