Carbenoid

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title: "Carbenoid" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["carbenes"] topic_path: "general/carbenes" source: "https://en.wikipedia.org/wiki/Carbenoid" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

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

:I-CH2-Zn-I

This complex reacts with an alkene to form a 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 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.

:[[Image:CarbenoidApplication.png|500px|Insertion of carbenoid into C-B bond]]

The enantiopurity of the chiral sulfoxide is preserved in the ultimate product after oxidation of the boronic ester to the alcohol indicating that a true carbene was never involved in the sequence.

References

References

  1. ''Organic Chemistry'' john McMurry Brooks /Cole Publishing Company 1988 {{ISBN. 0-534-07968-7
  2. 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

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carbenes