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Acid‐dependent selective formation of trans ‐aryl(germyl)ethenes or 1‐aryl‐1‐germylethenes by the protodestannylation of ( Z )‐germyl(stannyl)ethenes
Author(s) -
Nakano Taichi,
Senda Yoshiya,
Fukaya Kayo,
Sugiuchi Naoyuki,
Niimi Shinobu,
Takahashi Yutaka,
Kurihara Hiroyuki
Publication year - 2005
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.811
Subject(s) - chemistry , substituent , aryl , adduct , ring (chemistry) , iodide , medicinal chemistry , hydrochloric acid , stereochemistry , organic chemistry , alkyl
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. Copyright © 2005 John Wiley & Sons, Ltd.