Conversion of N-tosylsulfoximides to sulfoximines

US4113738A · kind A · utility

Assignee

• Polaroid Corporation · US

Inventors

• David H. Evans · Cambridge, US
• Richard B. Greenwald · Cambridge, US

Key dates

• Filing date: Apr 5, 1977
• Grant date: Sep 12, 1978
• Expiry date: Apr 5, 1997

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D339/08
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

This application is directed to a novel cleavage reaction whereby N-tosylsulfoximides of the following formula are converted to the corresponding sulfoximines. The relevant sulfoximides are represented by the formula: ##STR1## wherein R.sup.1 and R.sup.2 when taken individually (1) each represent an alkyl moiety containing up to 20 carbon atoms, unsubstituted with an alkali-stable group or (2) R.sup.1 is an alkyl moiety containing up to 20 carbon atoms and R.sup.2 is --(CH.sub.2).sub.n --S--R.sup.3 wherein n is greater than or equal to 2 and R.sup.3 is an alkyl moiety containing up to 20 carbon atoms and R.sup.1 and R.sup.2 when taken together represents (a) an alkylene moiety having 5 or 6 carbon atoms unsubstituted or substituted with an alkali-stable group; (b) --CH.sub.2 --.sub.x SO.sub.2 --CH.sub.2 -- wherein x is 3 or 4; or (c) --CHR--SO.sub.2 --CH.sub.2 CR'R"CH.sub.2 -- where R is hydrogen, or thioether R' and R" when taken individually are hydrogen or alkyl and R' and R" when taken together is a spiro group, preferably 1,3-dioxolane-2. This cleavage is accomplished by the use of ammonia and an alkali metal under defined reaction conditions which method affords a higher yiel…