Process for producing aryl alpha-haloalkyl sulfones

Details Process for producing aryl alpha-haloalkyl sulfones Process for producing aryl alpha-haloalkyl sulfones

1973-12-17

1976-04-06

Gotts, Lewis

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

C07C14906

Patent

active

039490017

ABSTRACT:
A process for preparing alkenes by reaction of various sulfone substrates with carbon tetrahalide in the presence of a strong base. The reactions are accelerated by the presence of a polar compound. Sulfone carbanions attack the carbon tetrahalide to produce an .alpha.-halogenated intermediate and a dihalocarbene. .alpha.-Halosulfones having .alpha.' hydrogens are converted to alkenes in situ via the Ramberg-Backland reaction. Sulfones having .alpha. but no .alpha.' hydrogens are simply .alpha.-halogenated. The dihalocarbene generated in the reaction may attack the product, solvent, or another substrate to form other products. Alkenes produced by reaction of carbon tetrahalides with di-sec-alkyl sulfones are readily attacked by dihalocarbene to form the alkene-dihalocarbene adduct (a substituted 1,1-dihalocyclopropane).

REFERENCES:
patent: 3830862 (1974-08-01), Meyers et al.
Goering et al., J.A.C.S. Vol. 79 pp. 2502-2506.
J. Org. Chem. Vol. 33 pp. 43-47.

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