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Proof of Inversion of Configuration on Stannylation of a Configurationally Stable, Tertiary Benzyllithium Compound from a Single‐Crystal X‐Ray Structure Analysis
Author(s) -
Hammerschmidt F.,
Hanninger A.,
Völlenke H.
Publication year - 1997
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.19970031022
Subject(s) - deprotonation , chemistry , toluene , single crystal , bromide , ether , walden inversion , crystallography , inversion (geology) , crystal structure , dipole , stereochemistry , organic chemistry , ion , paleontology , structural basin , biology
Configurationally stable, dipole‐stabilised benzyllithium compounds ( R )‐and ( S )‐ 1 b , prepared by deprotonation of the corresponding esters with s BuLi in toluene/di‐ethyl ether (5:1), reacted with (–)‐menthyldimethyltin bromide to afford the stannanes (–)‐ 3 and ( + )‐ 4 , respectively. A single‐crystal X‐ray structure analysis of compound (–)‐ 3 proved that stannylation occurred with inversion of the configuration at the benzylic centre, assuming retention for the deprotonation step. Lithio‐destannylation and deuteration with MeOD follow a retentive course.