Desulfurization with Raney Nickel. II. Sulfonamides

George R. Pettit, Raymond E. Kadunce

Research output: Contribution to journalArticle

24 Scopus citations

Abstract

Several representative alkyl halides have been condensed with sodium saccharin and the resulting 1,1,3-trioxo-2-alkylbenzo[d]isothiazolines (Ia-f) desulfurized using Raney nickel. Employing common desulfurization methods, the reduction reaction was found to give cyclohexylcarboxamides (e.g., IV) and under very mild conditions, benzamides (Va-e). In comparative alkylation reactions the sodium derivatives of benzenesulfonylbenzamide (IIa), N,N-dibenzenesulfonyloxamide (IIIa) and dibenzenesulfonamide (VIb) were, in general, less satisfactory than sodium saccharin. Reaction between benzenesulfonamide and dimethylformamide in the presence of either benzenesulfonyl chloride, benzoyl chloride, carbobenzoxy chloride, or phosphorus oxychloride was shown to yield N,N-dimethyl-N′-benzenesulfonylformamidine (VII).

Original languageEnglish (US)
Pages (from-to)4566-4570
Number of pages5
JournalJournal of Organic Chemistry
Volume27
Issue number12
DOIs
StatePublished - Dec 1 1962
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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