# Carbenoid

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In [chemistry](/source/Chemistry) a **carbenoid** is a [reactive intermediate](/source/Reactive_intermediate) that shares reaction characteristics with a [carbene](/source/Carbene).[1] In the [Simmons–Smith reaction](/source/Simmons%E2%80%93Smith_reaction) the carbenoid intermediate is a [zinc](/source/Zinc) / [iodine](/source/Iodine) [complex](/source/Complex_(chemistry)) that takes the form of

- I-CH2-Zn-I

This complex reacts with an [alkene](/source/Alkene) to form a [cyclopropane](/source/Cyclopropane) just as a carbene would do.

Carbenoids appear as intermediates in many other reactions. In one system a carbenoid chloroalkyllithium reagent is prepared in situ from a [sulfoxide](/source/Sulfoxide) and [t-BuLi](/source/Tert-Butyllithium) 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.[2]

The [enantiopurity](/source/Enantiopurity) of the chiral sulfoxide is preserved in the ultimate product after oxidation of the boronic ester to the [alcohol](/source/Alcohol_(chemistry)) indicating that a true carbene was never involved in the sequence.

## See also

- The silicon pendant: [Silylenoids](/source/Silylenoid)

## References

1. **[^](#cite_ref-1)** *Organic Chemistry* john McMurry Brooks /Cole Publishing Company 1988 [ISBN](/source/ISBN_(identifier)) [0-534-07968-7](https://en.wikipedia.org/wiki/Special:BookSources/0-534-07968-7)

1. **[^](#cite_ref-2)** Iterative Stereospecific Reagent-Controlled Homologation of Pinacol Boronates by Enantioenriched -Chloroalkyllithium Reagents Paul R. Blakemore and Matthew S. Burge [J. Am. Chem. Soc.](/source/J._Am._Chem._Soc.); **2007**; 129(11) pp 3068 - 3069; (Communication) [doi](/source/Doi_(identifier)):[10.1021/ja068808s](https://doi.org/10.1021%2Fja068808s)

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