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Updated: Jul 16, 2026

A Simple and Efficient Protocol for the Catalytic Insertion Polymerization of Functional Norbornenes
Published on: February 27, 2017
Vinyldiazolactone as a vinylcarbene precursor: Highly selective C-H insertion and cyclopropanation reactions
Darren Bykowski1, Kou-Hui Wu, Michael P Doyle
1Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland 20742, USA.
Abstract:
Vinylcarbenes are versatile synthetic intermediates, capable of asymmetric cyclopropanation and insertion into unactivated C-H bonds. The vinyldiazolactone precursor to the metal vinylcarbene possesses superior stability in comparison to previously known vinyldiazoacetates and, for the first time, allows the use of Z-vinylcarbenes in asymmetric C-H insertion and cyclopropanation reactions. Dirhodium azetidinone ligated compounds are optimal catalysts. Cyclopropanation coupled with the Cope rearrangement provides access to trans-3,4-disubstituted hydroazulenes.
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