X‐Ray Structure Analysis of α‐Lithiophenylacetonitrile · Lithium Diisopropyl amide· 2 Tetramethylethylenediamine—a “Quasi‐Dianion Complex” | Zendy

Zarges Wolfgang | Zendy; Marsch Michael | Zendy; Harms Klaus | Zendy; Boche Gernot | Zendy

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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.

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