A convenient direct synthesis of α-N,N-dialkylaminophosphonates under aprotic conditions

Phosphorus, Sulfur and Silicon and Related Elements

Volumn 113, Issue 1-4, 1996, Pages 299-301

  Malhiac, Catherine ^a   Combret, Jean Claude ^a   Boussad, Kamal ^a   Klein, Jean Louis ^a  

^a UNIVERSITÉ DE ROUEN   (France)

Author keywords

Dialkylaminosilanes; One pot aprotic reaction; N,N Dialkylaminophosphonates

Indexed keywords

EID: 0039748439     PISSN: 10426507     EISSN: None     Source Type: Journal    
DOI: 10.1080/10426509608046402     Document Type: Article

References (14)

1. (a) E. K. Baylis, C. D. Campbell and J. G. Dingwall, J. Chem. Soc., Perkin Trans I, 2845 (1984) and including references;
2. (b) P. Kafarski and P. Mastalerz, "Aminophosphonates": "Natural Occurrence Biochemistry and Biological Properties," Beiträge der Wirkstofforschung, Ak. Ind. Kompl. DDR, Vol. 21, 1984, pp. 32-83;
3. (c) L. Maier and P. J. Diel, Phosphorus, Sulfur and Silicon, 57, 57 (1991).
4. For a recent report on synthesis of various thiophenic derivatives see C. Hubert, B. Oussaid, G. Etemad-Moghadam, M. Koenig and B. Garrigues, Synthesis, 51 (1994) and references therein.
5. E. K. Fields, J. Amer. Chem. Soc., 74, 1528 (1952).
6. T. Morimoto, M. Aono and M. Sekiya, J. Chem. Soc., Chem. Commun., 1055 (1984); T. Morimoto, T. Takahashi and M. Sekiya, J. Chem. Soc., Chem. Commun., 794 (1984); A. A. Prishchenko, M. V. Livantsov, N. V. Boganova and I. F. Lutsenko, Zh. Obshch. Khim., 59, 2383 (1989); G. Courtois and L. Miginiac, Synth. Commun., 21, 201 (1991).
7. T. Morimoto, M. Aono and M. Sekiya, J. Chem. Soc., Chem. Commun., 1055 (1984); T. Morimoto, T. Takahashi and M. Sekiya, J. Chem. Soc., Chem. Commun., 794 (1984); A. A. Prishchenko, M. V. Livantsov, N. V. Boganova and I. F. Lutsenko, Zh. Obshch. Khim., 59, 2383 (1989); G. Courtois and L. Miginiac, Synth. Commun., 21, 201 (1991).
8. T. Morimoto, M. Aono and M. Sekiya, J. Chem. Soc., Chem. Commun., 1055 (1984); T. Morimoto, T. Takahashi and M. Sekiya, J. Chem. Soc., Chem. Commun., 794 (1984); A. A. Prishchenko, M. V. Livantsov, N. V. Boganova and I. F. Lutsenko, Zh. Obshch. Khim., 59, 2383 (1989); G. Courtois and L. Miginiac, Synth. Commun., 21, 201 (1991).
9. T. Morimoto, M. Aono and M. Sekiya, J. Chem. Soc., Chem. Commun., 1055 (1984); T. Morimoto, T. Takahashi and M. Sekiya, J. Chem. Soc., Chem. Commun., 794 (1984); A. A. Prishchenko, M. V. Livantsov, N. V. Boganova and I. F. Lutsenko, Zh. Obshch. Khim., 59, 2383 (1989); G. Courtois and L. Miginiac, Synth. Commun., 21, 201 (1991).
10. P. Aube, I. Christot, J.-C. Combret and J.-L. Klein, Bull. Soc. Chim. Fr., 1009 (1988).
11. 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).
12. 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.
13. C. Malhiac, J. C. Combret and A. Atmani, to be published.
14. C. Malhiac, Doctorat de Chimie, Rouen, France, 1993.