A CONVENIENT DIRECT SYNTHESIS OF α-N,N-DIALKYLAMINOPHOSPHONATES UNDER APROTIC CONDITIONS

References

• Baylis , E. K. , Campbell , C. D. and Dingwall , J. G. 1984 . J. Chem. Soc., Perkin Trans I , : 2845 and including references
   Google Scholar
• Kafarski , P. and Mastalerz , P. 1984 . Aminophosphonates”: “Natural Occurrence Biochemistry and Biological Properties , Vol. 21 , 32 – 83 . Beiträge der Wirkstofforschung, Ak. Ind. Kompl. DDR .
   Google Scholar
• Maier , L. and Diel , P. J. 1991 . Phosphorus. Sulfur and Silicon , 57 : 57
   Web of Science ®Google Scholar
• Hubert , C. , Oussaid , B. , Etemad-Moghadam , G. , Koenig , M. and Garrigues , B. 1994 . Synthesis , : 51 For a recent report on synthesis of various thiophenic derivatives see, and references therein
   Web of Science ®Google Scholar
• Fields , E. K. 1952 . J. Amer Chem. Soc. , 74 : 1528
   Web of Science ®Google Scholar
• Morimoto , T. , Aono , M. and Sekiya , M. 1984 . J. Chem. Soc., Chem. Commun. , : 1055
   Google Scholar
• Morimoto , T. , Takahashi , T. and Sekiya , M. 1984 . J. Chem. Soc., Chem. Commun. , : 794
   Google Scholar
• Prishchenko , A. A. , Livantsov , M. V. , Boganova , N. V. and Lutsenko , I. F. 1989 . Zh. Obshch. Khim. , 59 : 2383
   Google Scholar
• Courtois , G. and Miginiac , L. 1991 . Synth. Commun. , 21 : 201
   Web of Science ®Google Scholar
• Aube , P. , Christot , I. , Combret , J.-C. and Klein , J.-L. 1988 . Bull. Soc. Chim. Fr. , : 1009
   Google Scholar
• Satisfactory microanalysis (C ± 0.28, H ± 0.25, N ± 0.30) as well as spectroscopic data in good agreement with assigned structures obtained for all new products 5. Data 1H NMR (in ppm): 5a: 2.25 (s, 6H), 3.30 (d, 3H, J = 10 Hz), 3.70 (d, 3H, J = 10 Hz), 3.75 (d, 1H, J = 24 Hz), 7.25 (m, 5H); 5b: 2.40 (s, 6H), 3.50 (d, 3H, J = 10 Hz), 3.90 (d, 3H, J = 10 Hz), 3.95 (d, 1H, J = 24 Hz), 7.50 (m, 2H), 8.70 (m, 2H); 5c: 2.30 (s, 6H), 3.55 (d, 3H, J = 10 Hz), 3.80 (d, 3H, J = 10 Hz), 3.95 (d, 1H, J = 24 Hz), 6.40 (m, 2H). 7.40 (m. 1H); 5d: 2.35 (s, 6H), 3.50 (d, 3H, J = 10 Hz), 3.85 (d, 3H, J = 10 Hz), 4.10 (d, 1H, J = 24 Hz), 7.25 (m. 3H); 5e: 2.70 (m, 4H), 3.40 (d, 3H, J=10 Hz), 3.80 (d, 3H, J = 10 Hz), 3.65 (m, 5H), 7.30 (m, 5H); 5f: 1.20 (dd, 3H, J = 7 Hz, 18 Hz), 2.75 (m, 5H), 3.60 (m, 4H), 3.70 (d, 3H, J = 11 Hz), 3.80 (d, 3H, J = 11 Hz); 5g: 0.95 (d, 3H), 1.00 (d, 3H), 2.40 (d, 6H), 2.60 (dd, 1H, J = 7 Hz, 15 Hz). 3.60 (d, 3H, J = 11 Hz). 3.70 (d, 3H, J = 10 Hz); 5h: 2.75 (m, 5H), 3.65 (m, 4H), 3.80 (d. 3H, J = 11 Hz), 3.90 (d, 3H, J = 11 Hz), 4.10 (d, 2H), 7.2 (m, 5H); 5i: 2.50 (s, 6H), 3.75 (d, 3H, J = 11 Hz), 3.85 (d, 3H, J = 11 Hz), 3.80 (m, 1H), 6.35 (ddd, 1H, J = 15 Hz, 10 Hz, 7 Hz), 6.65 (dd, 1H, J = 16 Hz, 3 Hz), 7.40 (m, 5H)
   Google Scholar
• All compounds exhibit analogous characteristic MS data with a major fragmentation path of molecular ion (loss of phosphorous group) leading to a iminium moiety (an easy loss of the benzyl group also occurs for 5h); all other fragments are very weak with however molecular ion being always noticeable
   Google Scholar
• Malhiac , C. , Combret , J. C. and Atmani , A. to be published
   Google Scholar
• Malhiac , C. 1993 . Doctorat de Chimie Rouen, , France
   Google Scholar