Reaction of Alkyl Sulfoxides and Phenylphosphinic Acid with Amines. Alternative Reagents for Secondary Amines N-Alkylation

References

• Moore , M. L. 1949 . Organic Reactions , Vol. 5 : 301
   Google Scholar
• Ito , K. , Oba , H. and Sekiya , M. 1976 . Bull. Chem. Soc. Jpn. , 49 : 2485
   Google Scholar
• Lukasiewicz , A. 1963 . Tetrahedron , 19 : 178
   Google Scholar
• Meiners , A. F. , Bolze , C. , Sherer , C. A. L. and Morris , F. V. 1958 . J. Org. Chem. , 23 : 1122
   Web of Science ®Google Scholar
• Pine , S. H. and Sanchez , B. L. 1971 . J. Org. Chem. , 36 : 829
   Web of Science ®Google Scholar
• Sondengam , B. L. , Hentchoya Hemo , J. and Charles , G. 1973 . Tetrahedron Lett. , 14 : 261
   Google Scholar
• Borch , R. F. and Hassid , A. J. 1972 . J. Org. Chem. , 37 : 1673
   Web of Science ®Google Scholar
• Watanabe , K. and Wakabayashi , T. 1980 . J. Org. Chem. , 45 : 357
   Google Scholar
• Abdel-Magid , A. F. , Maryanoff , C. A. and Carson , K. G. 1990 . Tetrahedron Lett. , 31 : 5598
   Google Scholar
• Abdel-Magid , A. F. , Mayanoff , C. A. and Bobovski , G. 1985 . J. Org. Chem. , 50 : 929
   Google Scholar
• Fülöp , F. , Pimlaja , K. , Mattinen , J. and Bernath , G. 1987 . Tetrahedron Lett. , 28 : 115
   Google Scholar
• Ram , S. and Spicer , L. D. 1989 . Synthetic commun. , 19 : 3561
   Web of Science ®Google Scholar
• Barton , D. H. R. , Hervé , Y. , Potier , P. and Thierry , J. 1986 . Tetrahedron , 42 : 4983 However mandelic acid and mandelate ammonium do not react. Here, the phenylglycine decarboxilation process probably involves phenylphosphinic acid, whereas aminoacids can be decarboxilated according to a one-electron transfer mecanism see
   Web of Science ®Google Scholar
• Agami , C. 1965 . Bull. Soc. Chim. France , 67
   Google Scholar
• Kenney , W. J. , Walsh , J. A. and Davenport , D. A. 1961 . J. Am. Chem. Soc. , 83 : 4019
   Web of Science ®Google Scholar
• Nace , H. R. and Monagle , J. J. 1959 . J. Org. Chem. , 24 : 1792
   Web of Science ®Google Scholar
• Mancuso , A. J. and Swern , D. 1981 . Synthesis , : 165
   Web of Science ®Google Scholar
• Traynellis , V. J. and Hergenrother , W. L. 1964 . J. Org. Chem. , 29 : 221
   Google Scholar
• Dhavan , B. and Redmore , D. 1988 . J. Chem. Research. , : 34
   Google Scholar
• Hanessian , S. , Yang-Chung , G. , Lavalle , P. and Pernet , A. G. 1972 . J. Am. Chem. Soc. , 94 : 8929 A related mechanism has been envisioned for the reaction of alcohols with DMSO yielding methylene acetals under NBS catalysis see
   Web of Science ®Google Scholar
• Chauvin , R. 1990 . Tetrahedron: Asymmetry , 1 : 737
   Google Scholar