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Unusual Formation of an Azaphospholene from 1,3,4,5‐Tetramethylimidazol‐2‐ylidene and Di(isopropyl)aminophosphaalkyne
Author(s) -
Hahn F. Ekkehardt,
Le Van Duc,
Moyes Michelle C.,
von Fehren Thorsten,
Fröhlich Roland,
Würthwein ErnstUlrich
Publication year - 2001
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/1521-3773(20010903)40:17<3144::aid-anie3144>3.0.co;2-f
Subject(s) - isopropyl , intramolecular force , carbene , substituent , adduct , chemistry , yield (engineering) , density functional theory , medicinal chemistry , computational chemistry , stereochemistry , organic chemistry , physics , thermodynamics , catalysis
Intramolecular C−H insertion into the methyl group of the amino substituent of 1 is shown by density functional theory calculations to stabilize this intermediate in the formation of the novel 1:1 carbene–phosphaalkyne adduct 2 . Compound 2 is formed in near quantitative yield by reaction of 1,3,4,5‐tetramethylimidazol‐2‐ylidene with P≡CN i Pr 2 .