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[ tert ‐Butylcyanide · Lithium Bis(trimethylsilyl)amide] 2 , a Model of the Intermediate RCN. MR′ Complex Formed in Reactions of Cyanides RCN with Organometallic Compounds R′M
Author(s) -
Boche Gernot,
Langlotz Ira,
Marsch Michael,
Harms Klaus,
Frenking Gernot
Publication year - 1993
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.199311711
Subject(s) - chemistry , lithium (medication) , amide , intramolecular force , ab initio , trimethylsilyl , lithium amide , group 2 organometallic chemistry , computational chemistry , medicinal chemistry , stereochemistry , organic chemistry , catalysis , molecule , medicine , enantioselective synthesis , endocrinology
The dialkylation and dideuteration of cyanides are proposed to proceed through intermediates of the type RR′CHCN · LiR″. The title compound 1 (central framework shown on the right) is the first structurally characterized compound of this type. The results of ab initio calculations on the model compound H 3 CCN · LiNH 2 are in agreement with the high stability and the energetically favorable intramolecular proton shift found experimentally.