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X‐Ray Structure Analysis of α‐Lithiophenylacetonitrile · Lithium Diisopropyl amide· 2 Tetramethylethylenediamine—a “Quasi‐Dianion Complex”
Author(s) -
Zarges Wolfgang,
Marsch Michael,
Harms Klaus,
Boche Gernot
Publication year - 1989
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198913921
Subject(s) - lithium diisopropylamide , adduct , tetramethylethylenediamine , chemistry , halide , base (topology) , amide , alkyl , lithium (medication) , lithium amide , molar ratio , polymer chemistry , medicinal chemistry , organic chemistry , catalysis , ion , deprotonation , medicine , mathematical analysis , mathematics , enantioselective synthesis , endocrinology
The authors report the first structural characterization of the adduct formed between a monoanion and a base, such as that formed by reaction of a carbon acid (here, phenylacetonitrile) with ≥2 molar equivalents of base (here, lithium diisopropylamide)— namely, “QUADAC” ( 1 .2 TMEDA). It reacts as a “dianion” with alkyl halides and D 2 O to give dialkylated and dideuterated products, respectively.