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N‐Heterocyclic Carbene Coordinated Neutral and Cationic Heavier Cyclopropylidenes
Author(s) -
Jana Anukul,
Omlor Isabell,
Huch Volker,
Rzepa Henry S.,
Scheschkewitz David
Publication year - 2014
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/anie.201405238
Subject(s) - carbene , allene , chemistry , cyclopropene , cationic polymerization , isomerization , silylene , medicinal chemistry , silicon , stereochemistry , dissociation (chemistry) , ring (chemistry) , crystallography , propyne , photochemistry , polymer chemistry , catalysis , organic chemistry
Cyclopropylidene is a transient intermediate of the allene–propyne–cyclopropene isomerization. The incorporation of heavier Group 14 elements into the cyclopropylidene scaffold has to date been restricted to the formal replacement of the carbenic carbon atom by a base‐coordinated silicon(II) center. Herein we report the synthesis and characterization of NHC‐coordinated heavier cyclopropylidenes (Si 2 GeR 3 X, and Si 3 R 3 Br; X=Cl, Mes; R=Tip=2,4,6‐ i Pr 3 C 6 H 2 ) in which the three‐membered ring is exclusively formed by silicon and germanium. In case of the chloro‐substituted Si 2 Ge‐cyclopropylidene, a stable heavier cycloprop‐1‐yl‐2‐ylidene cation is obtained by NHC‐induced chloride dissociation.