Unusual Formation of an Azaphospholene from 1,3,4,5-Tetramethylimidazol-2-ylidene and Di(isopropyl)aminophosphaalkyne

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‐...

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Published inAngewandte Chemie International Edition Vol. 40; no. 17; pp. 3144 - 3148
Main Authors Hahn, F. Ekkehardt, Le Van, Duc, Moyes, Michelle C., von Fehren, Thorsten, Fröhlich, Roland, Würthwein, Ernst-Ulrich
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag GmbH 03.09.2001
WILEY‐VCH Verlag GmbH
Wiley
Subjects
carbenes
Chemistry
Chemistry, Multidisciplinary
density functional calculations
insertion
phosphaalkynes
phosphorus heterocycles
Physical Sciences
Science & Technology
density functional calculations
NUCLEOPHILIC CARBENES
1,2,4-TRIPHOSPHOLE
carbenes
insertion
phosphaalkynes
phosphorus heterocycles
PHOSPHAALKENES
DERIVATIVES
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Summary: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≡CNiPr2.
Bibliography:ark:/67375/WNG-7TD5H42D-4
ArticleID:ANIE3144
istex:93E3A14517DC0EA0D1DB1F21DA4B448F862EFB34
This project was supported by the Deutsche Forschungsgemeinschaft and the Fonds der Chemischen Industrie.
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1433-7851
1521-3773
DOI:10.1002/1521-3773(20010903)40:17<3144::AID-ANIE3144>3.0.CO;2-F