Synthesis of an Extremely Bent Acyclic Allene (A "Carbodicarbene"): A Strong Donor Ligand

Pushed to the limit: Pushing CC π bonds to the breaking point by using a push–push substitution pattern forces allenes to bend (see structure; C light blue, N dark blue). An acyclic allene featuring a CCC bond angle of 134.8° has been isolated in which the typically sp‐hybridized central carbon a...

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Published inAngewandte Chemie (International ed.) Vol. 47; no. 17; pp. 3206 - 3209
Main Authors Dyker, C. Adam, Lavallo, Vincent, Donnadieu, Bruno, Bertrand, Guy
Format Journal Article
LanguageEnglish
Published Weinheim Wiley-VCH Verlag 14.04.2008
WILEY-VCH Verlag
WILEY‐VCH Verlag
Wiley
Subjects
allenes
carbenes
Chemistry
Chemistry, Multidisciplinary
donor-acceptor systems
Physical Sciences
Science & Technology
structure elucidation
allenes
donor-acceptor systems
RHODIUM
REPLIQUE
COMPLEXES
carbenes
X-RAY
CHEMISTRY
TRISILAALLENE
structure elucidation
N-HETEROCYCLIC CARBENES
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Summary:Pushed to the limit: Pushing CC π bonds to the breaking point by using a push–push substitution pattern forces allenes to bend (see structure; C light blue, N dark blue). An acyclic allene featuring a CCC bond angle of 134.8° has been isolated in which the typically sp‐hybridized central carbon atom approaches a configuration that has two lone pairs of electrons, and acts as a very strong η1‐donor ligand for transition metals.
Bibliography:http://dx.doi.org/10.1002/anie.200705620
NSERC
ACS
ArticleID:ANIE200705620
ark:/67375/WNG-19WBD3F0-T
NSF - No. CHE 0518675
We are grateful to the NSF (CHE 0518675) for financial support of this work, the NSERC for a postdoctoral fellowship (C.A.D.), and the ACS for a graduate fellowship (V.L.).
istex:DA4AF4044669D8F0BAA8822C74F8E742D1819914
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200705620