Walter Wendell Matthews

US Patent:

39534944, Apr 27, 1976

Filed:

Dec 14, 1970

Appl. No.:

5/098078

Inventors:

Cal Yale Meyers - Carbondale IL
Walter Sidney Matthews - Carbondale IL

Assignee:

Southern Illinois University Foundation - Carbondale IL

International Classification:

C07C 5128
C07C 6742

US Classification:

260468R

Abstract:

A process for preparing aldehydes, ketones, carboxylic acids and esters by reaction of various substrates with carbon tetrahalides in the presence of a strong base. The reactions are accelerated by the presence of a polar solvent. Anions of the substrate attack the carbon tetrahalide to produce a halogenated intermediate and a dihalocarbene. The halogenated intermediate reacts with the base to form the indicated products. By the reactions of this process, primary alcohols are converted to aldehydes, carboxylic acids and esters, secondary alcohols are converted to ketones and ketones having an. alpha. -methyl group or both. alpha. and. alpha. ' hydrogens are converted to carboxylic acids and esters. Non. alpha. -methyl ketones having. alpha. but no. alpha. ' hydrogens are simply. alpha.

US Patent:

39490017, Apr 6, 1976

Filed:

Dec 17, 1973

Appl. No.:

5/425294

Inventors:

Cal Yale Meyers - Carbondale IL
Walter Sidney Matthews - Carbondale IL
Ashok M. Malte - Poona, IN

Assignee:

Southern Illinois University Foundation - Carbondale IL

International Classification:

C07C14906

US Classification:

260607A

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).