Exploring Two Reactions of Ketones with Ge[CH(SiMe3)2]2:  CH and OH Insertion

Herein we report the CH insertion of a stable germylene, Ge[CH(SiMe3)2]2, into the α-CH bonds of the acetyl-containing ketones acetone, butanone, and cyclopropyl methyl ketone. This CH insertion reaction requires the presence of MgCl2, yet the reaction can be successfully carried out in hydrocarbon,...

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Bibliographic Details
Published in:Organometallics 2003-11, Vol.22 (24), p.5054-5062
Main Authors: Sweeder, Ryan D, Miller, Karla A, Edwards, Fern A, Wang, Jia, Banaszak Holl, Mark M, Kampf, Jeff W
Format: Article
Language:English
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Summary:Herein we report the CH insertion of a stable germylene, Ge[CH(SiMe3)2]2, into the α-CH bonds of the acetyl-containing ketones acetone, butanone, and cyclopropyl methyl ketone. This CH insertion reaction requires the presence of MgCl2, yet the reaction can be successfully carried out in hydrocarbon, aromatic, and ethereal solvents. In the absence of MgCl2, these acetyl-containing ketones do not undergo CH insertion but instead undergo an OH insertion to give a germyl vinyl ether. A number of other ketones, including the acetyl-containing pinacolone, have been observed to only undergo insertion into the OH bond even in the presence of MgCl2.
ISSN:0276-7333
1520-6041
DOI:10.1021/om030308+