Protonation of sulfinamides. Does it occur at oxygen or nitrogen?

Journal of Organic Chemistry

Volumn 61, Issue 21, 1996, Pages 7593-7596

  Bujnicki, Bogdan ^a   Drabowicz, Józef ^a   Mikołajczyk, Marian ^a   Kolbe, Alfred ^b   Stefaniak, Lech ^c  

^a CENTRE OF MOLECULAR AND MACROMOLECULAR STUDIES   (Poland)

^b MARTIN LUTHER UNIVERSITY HALLE WITTENBERG   (Germany)

^c INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000674490     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960205j     Document Type: Article

References (32)

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7. (7) The results were presented at the IX International Conference on the Organic Chemistry of Sulfur, Merseburg, Germany, 1994. Bujnicki, B.; Drabowicz, J.; Mikołajczyk, M.; Kolbe, A. Phosphorus, Sulfur, Silicon Relat. Elem. 1994, 95, 419.
8. (7) The results were presented at the IX International Conference on the Organic Chemistry of Sulfur, Merseburg, Germany, 1994. Bujnicki, B.; Drabowicz, J.; Mikołajczyk, M.; Kolbe, A. Phosphorus, Sulfur, Silicon Relat. Elem. 1994, 95, 419.
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24. For conclusive X-ray evidence for O-methylation of sulfinamides by methyl triflate, see: Pickersgill, I. F.; Marchington, A. P.; Thornton-Pett, M; Rayner, C. M. Chem. Commun. 1995, 647.
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27. 1. The upfield shift of these carbons in morpholine was Δδ = 4.35 and 3.19 ppm, respectively. The corresponding values for α-phenylethylamine were 6.46 and 2.47 ppm.
28. Protonation on nitrogen was also assumed in studies of pK values of sulfenamides and sulfinamides: Bayfield, R. F.; Cole, E. R. Phosphorus, Sulfur, Silicon Relat. Elem. 1989, 45, 237. Clarke, V.; Cole, E. R. Phosphorus, Sulfur, Silicon Relat. Elem. 1989, 45, 243.
29. Protonation on nitrogen was also assumed in studies of pK values of sulfenamides and sulfinamides: Bayfield, R. F.; Cole, E. R. Phosphorus, Sulfur, Silicon Relat. Elem. 1989, 45, 237. Clarke, V.; Cole, E. R. Phosphorus, Sulfur, Silicon Relat. Elem. 1989, 45, 243.
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