In chemistry a carbenoid is a reactive intermediate that shares reaction characteristics with a carbene. In the Simmons–Smith reaction the carbenoid intermediate is a zinc / iodine complex that takes the form of
Carbenoids appear as intermediates in many other reactions. In one system a carbenoid chloroalkyllithium reagent is prepared in situ from a sulfoxide and t-BuLi which reacts the boronic ester to give an ate complex. The ate complex undergoes a 1,2-metallate rearrangement to give the homologated product, which is then further oxidised to a secondary alcohol.
- The silicon pendant: Silylenoids
- Organic Chemistry john McMurry Brooks /Cole Publishing Company 1988 ISBN 0-534-07968-7
- Iterative Stereospecific Reagent-Controlled Homologation of Pinacol Boronates by Enantioenriched -Chloroalkyllithium Reagents Paul R. Blakemore and Matthew S. Burge J. Am. Chem. Soc.; 2007; 129(11) pp 3068 - 3069; (Communication) doi:10.1021/ja068808s