Conversion of N-tosylsulfoximides to sulfoximines

Details Conversion of N-tosylsulfoximides to sulfoximines Conversion of N-tosylsulfoximides to sulfoximines

1977-04-05

1978-09-12

Jaisle, Cecilia M.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260551S, C07D33908

Patent

active

041137388

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 yield of sulfoximine and a product which is thereby more readily isolated and purified.

REFERENCES:
patent: 2648705 (1953-08-01), Reiner
patent: 3255116 (1966-06-01), Berry
patent: 3376338 (1968-04-01), Anderson
patent: 3557206 (1971-01-01), Lyness
patent: 3637664 (1972-01-01), Satzinger
patent: 3654359 (1972-04-01), Grosselink
patent: 3868418 (1975-02-01), Herrmann
patent: 3919310 (1975-11-01), Herrmann

Affiliated with

Also associated with

Rating

Conversion of N-tosylsulfoximides to sulfoximines does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Conversion of N-tosylsulfoximides to sulfoximines, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Conversion of N-tosylsulfoximides to sulfoximines will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2383889