Carbenoid

Summary

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. 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.

Official source

https://en.wikipedia.org/wiki/Carbenoid

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Related publications (2)

Efficient Kinetic Resolution of Sulfur-Stereogenic Sulfoximines by Exploiting (CpRhIII)-Rh-X-Catalyzed C-H Functionalization

Nicolai Cramer, Marcus Brauns

Chiral sulfoximines with stereogenic sulfur atoms are promising motifs in drug discovery. We report an efficient method to access chiral sulfoximines through a C-H functionalization based kinetic resolution. A rhodium(III) complex equipped with a chiral Cp ...

WILEY-V C H VERLAG GMBH2019

Alkyl/halogen substitution in carbenes (carbenoids): a route to new cyclopropane derivatives

7-Halo-7-methylnorcaranes (I) and 7,7-dimethylnorcarane (II) are formed via replacement of halogen by Me during the reaction of cyclohexene (III) with carbenes (carbenoids) and MeLi. Thus, III is treated with CHClF2 or CCl2F2 and MeLi to give a mixt. of 7- ...

1971

Related concepts (1)

Cyclopropanation

In organic chemistry, cyclopropanation refers to any chemical process which generates cyclopropane () rings. It is an important process in modern chemistry as many useful compounds bear this motif; for example pyrethroid insecticides and a number of quinolone antibiotics (ciprofloxacin, sparfloxacin, etc.). However, the high ring strain present in cyclopropanes makes them challenging to produce and generally requires the use of highly reactive species, such as carbenes, ylids and carbanions.