Mechanism of Rhodium-Catalyzed Carbene Formation from Diazo Compounds

Authors

Freeman M. Wong
Jianbo Wang
Alvan C. Hengge, Utah State UniversityFollow
Weiming Wu

Document Type

Article

Journal/Book Title

Organic Letters

Publication Date

2007

Volume

9

Issue

9

First Page

1663

Last Page

1665

Abstract

A large and normal nitrogen-15 kinetic isotope effect of 1.035 ± 0.003 provides direct support for the proposed mechanism for the rhodium-catalyzed carbene formation from diazo compounds, which involves the fast formation of a metal−diazo complex followed by rate-limiting extrusion of N₂. The large magnitude of the KIE indicates extensive C−N bond fission in the transition state.

Recommended Citation

Freeman M. Wong, Jianbo Wang, Alvan C. Hengge, and Weiming Wu “Mechanism of Rhodium- Catalyzed Carbene Formation from Diazo Compounds.” Org. Lett.; 2007; 9(9); 1663-1665.