Selective nitration of styrenes with clayfen and clayan: A solvent-free synthesis of β-nitrostyrenes

Tetrahedron Letters

Volumn 39, Issue 23, 1998, Pages 3977-3980

  Varma, Rajender S ^a   Naicker, Kannan P ^a   Liesen, Per J ^a  

^a SAM HOUSTON STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

REAGENT; STYRENE DERIVATIVE;

ARTICLE; CLAY; NITRATION; SYNTHESIS;

EID: 0032482522     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00740-0     Document Type: Article

References (47)

1. 1. (a) Perekalin, V.V.; Lipina, E.S.; Berestovitskaya, V.M.; Efremov, D.A. Nitroalkenes, Conjucated Nitro Compounds; John Wiley, Chichester, 1994; Chapter 2, pp 53-168;
2. (b) Ono, N. In Organic Nitro Chemistry Series, Nitro Compounds, Recent Advances in Synthesis and Chemistry; Feuer, H.; Nielsen, A.T.; Eds.; VCH, N.Y., 1990; Chap. 1, pp 1-135;
3. (c) Barrett, A.G.M. Chem. Soc. Rev. 1991, 20, 95;
4. (d) Kabalka, G.W.; Guindi, L.H.M.; Varma, R.S. Tetrahedron 1990, 46, 7443;
5. (e) Kabalka, G.W.; Varma, R.S. Org. Prep. Proc. Int. 1987, 19, 283.
6. 2. Shulgin, A.T. J. Med. Chem. 1966, 9, 45.
7. 3. Grebenyuk, A.D.; Ismailova, R.A.; Tokbolatov, R.B.; Ovadova, T. Zh. Org. Khim. 1990, 26, 680.
8. 4. Sy, W.W.; By, A.W, Tetrahedron Lett. 1985, 26, 1193.
9. 5. (a) Masnovi, J.M.; Kochi, J.K. Recl. Trav. Chim. Pays-Bas 1986, 105, 286;
10. (b) Penczek, S.; Jagur-Grodzinski, J.; Szwarc, M. J. Am. Chem. Soc. 1968, 90, 2174;
11. (c) Schmidt, E.; Fischer, H. Chem. Ber. 1920, 53, 1529.
12. 6. Tinsley, S.W. J. Org. Chem. 1961, 26, 4723.
13. 7. Corey, E.J.; Estreicher, H. J. Am. Chem. Soc. 1978, 100, 6294.
14. 8. Mathew, L.; Varghese, B.; Sankararaman, S. J. Chem. Soc., Perkin Trans. 2 1993, 2399.
15. 9. Hayama, T.; Tomoda, S.; Takeuchi, Y.; Normura, Y. Tetrahedron Lett. 1982, 23, 4733.
16. 10. Jew, S.-S.; Kim, H.-D.; Cho, Y.-S.; Cook, C-H. Chem. Lett. 1986, 1747.
17. 11. Hwu, J.R.; Chen, K.-L.; Ananthan, S. J. Chem. Soc., Chem. Commun. 1994, 1425.
18. 12. (a) Hata, E.; Yamada, T.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1995, 68, 3626;
19. (b) Mukaiyama, T.; Hata, E.; Yamada, T. Chem. Lett. 1995, 505.
20. 13. For cleavage-deprotection reactions see: (a) Varma, R.S.; Meshram, H.M. Tetrahedron Lett. 1997, 38, 5427;
21. (b) Varma, R.S.; Saini, R.K. Tetrahedron Lett. 1997, 38, 2623;
22. (c) Varma, R.S.; Varma, M.; Chatterjee, A.K. J. Chem. Soc., Perkin. Trans. 1, 1993, 999;
23. (d) Varma, R.S.; Chatterjee, A.K.; Varma, M. Tetrahedron Lett. 1993, 34, 3207;
24. (e) Varma, R.S.; Lamture, J.B.; Varma, M. Tetrahedron Lett. 1993, 34, 3029;
25. (f) Varma, R.S.; Chatterjee, A.K.; Varma, M. Tetrahedron Lett. 1993, 34, 4603;
26. (g) Varma, R.S.; Dahiya, R.; Saini, R.K. Tetrahedron Lett. 1997, 38, 8819;
27. (h) Varma, R.S.; Meshram, H.M. Tetrahedron Lett. 1997, 38, 7973. For condensation-cyclization reactions see:
28. (i) Varma, R.S.; Dahiya, R.; Kumar, S. Tetrahedron Lett. 1997, 38, 5131;
29. (j) Varma, R.S.; Saini, R.K. Synlett 1997, 857;
30. (k) Varma, R.S.; Dahiya, R. Synlett, 1997, 1245;
31. (l) Varma, R.S.; Dahiya, R.; Kumar, S. Tetrahedron Lett. 1997, 38, 2039. For oxidation reactions see:
32. (m) Varma, R.S.; Dahiya, R. Tetrahedron Lett. 1997,38, 2043;
33. (n) Varma, R.S.; Saini, R.K.; Meshram, H.M. Tetrahedron Lett. 1997,38, 6525;
34. (o) Varma, R.S.; Dahiya, R.; Saini, R.K. Tetrahedron Lett. 1997, 38, 7029;
35. (p) Varma, R.S.; Saini, R.K.; Dahiya, R. Tetrahedron Lett. 1997, 38, 7823;
36. (q) Varma, R.S.; Dahiya, R.; Kumar, D. Molecules Online 1998, 2, 82;
37. (r) Varma, R.S.; Dahiya, R. Tetrahedron Lett. 1998, 39, 1307;
38. (s) Varma, R.S.; Saini, R.K. Tetrahedron Lett. 1998, 39, 1481;
39. (t) Varma, R.S.; Saini, R.K.; Dahiya, R. J. Chem. Res. (S) 1998, in press;
40. For reduction reactions see: (u) Varma, R.S.; Saini, R.K. Tetrahedron Lett. 1997, 38, 4337;
41. (v) Varma, R.S.; Naicker, K.P. Molecules Online 1998, 2, 94.
42. 14. (a) Cornelis, A.; Laszlo, P.; Pennetreau, P. J. Org. Chem. 1983, 48, 4771;
43. (b) Cornelis, A.; Laszlo, P.; Pennetreau, P. Bull. Soc. Chim. Belg. 1984, 93, 961;
44. (c) Balogh, M.; Pennetreau, P.; Hermecz, I.; Gerstmans, A. J. Org. Chem. 1990, 55, 6198.
45. 15. Meshram, H.M.; Reddy, G.S. Yadav, J.S. Tetrahedron Lett. 1997, 38, 8891.
46. 16. Suzuki, H.; Mori, T. J. Org. Chem. 1997, 62, 6498.
47. 17. Alumina bath (neutral alumina: 125 g, mesh ∼150, Aldrich; bath: 5.7 cm diameter) has three functions: (i) serves as a heat sink in the MW chamber; (ii) houses the small reaction vessels, and (iii) allows the easy measurement of the bulk temperature after completion of the reaction.