Acid‐dependent selective formation of  trans ‐aryl(germyl)ethenes or 1‐aryl‐1‐germylethenes by the protodestannylation of ( Z )‐germyl(stannyl)ethenes | Zendy

Nakano Taichi | Zendy; Senda Yoshiya | Zendy; Fukaya Kayo | Zendy; Sugiuchi Naoyuki | Zendy; Niimi Shinobu | Zendy; Takahashi Yutaka | Zendy; Kurihara Hiroyuki | Zendy

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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.

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