Desulfurization with Raney nickel. II. Sulfonamides

George Pettit, Raymond E. Kadunce

Research output: Contribution to journalArticle

25 Citations (Scopus)

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
StatePublished - 1962
Externally publishedYes

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Saccharin
Sulfonamides
Desulfurization
Nickel
Benzamides
Dimethylformamide
Alkylation
Sodium
Derivatives
benzenesulfonamide
carbobenzoxy chloride
phosphoryl chloride
benzenesulfonyl chloride
benzoyl chloride

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Desulfurization with Raney nickel. II. Sulfonamides. / Pettit, George; Kadunce, Raymond E.

In: Journal of Organic Chemistry, Vol. 27, No. 12, 1962, p. 4566-4570.

Research output: Contribution to journalArticle

Pettit, George ; Kadunce, Raymond E. / Desulfurization with Raney nickel. II. Sulfonamides. In: Journal of Organic Chemistry. 1962 ; Vol. 27, No. 12. pp. 4566-4570.
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AB - 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).

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