FORMATION OF SULFINAMIDES AND SULFONAMIDES BEARING THE ORGANO-AMINOMETHYLENE-DIMETHYLPHOSPHINE OXIDE OR SULFIDE GROUP

• Published in: Phosphorus, sulfur, and silicon and the related elements Vol. 122; no. 1; pp. 33 - 47
• Main Authors: Kaukorat, Thomas, Neda, Ion, Jones, Peter G., Schmutzler, Reinhard
• Format: Journal Article
• Language: English
• Published: Taylor & Francis Group 01.03.1997
• Subjects: Aminomethylene-dimethylphosphine oxide; n.m.r. spectra; sulfide; sulfinamides; sulfonamides; X-ray crystal Structure determinations
• ISSN: 1042-6507; 1563-5325
• DOI: 10.1080/10426509708043493

The reaction of N-methyl-N-trimethylsilylaminomethylene-dimethylphosphine oxide 1 and sulfide 2 with various sulfinyl and sulfonyl chlorides furnished, in good yield, a series of phosphorus-containing sulfinamides and sulfonamides. All, bearing the dimethylphosphoryl and thiohosphoryl group, respectively. All sulfinamides (3-8) show a complicated splitting pattern for the 1 H-n.m.r. resonances of the CH 2 P-group, due to the presence of a chiral sulfur atom. For the same reason, doubling of the ( CH 3 ) 2 P-proton resonances is observed for 3, 4, 7 and 8. N.m.r. spectra for the sulfonamides 9-11 are in accord with expectation. N-benzylaminomethylene-dimethylphosphine oxide 12 was allowed to react with chlorosulfonyl-acetic acid methyl ester in the presence of triethylamine as a base to form the phosphorus-containing sulfonamide 13 in good yield. In the reaction of 5 with air/moisture, by an unknown reaction course, the phosphorus-containing ammonium hydrogen sulfate 14 was formed. X-ray crystal structure determinations were conducted for 10 and 14. The two independent molecules of 10 are closely similar and show C-N-S-C torsion angles of 89, 83°. In compound 14, hydrogen bonding links two formula units.