Synthesis of a hindered C2-symmetric hydrazine and diamine by a crisscross cycloaddition of citronellal azine

Canadian Journal of Chemistry

Volumn 84, Issue 10, 2006, Pages 1242-1249

  Snider, Barry B ^a   Grabowski, James F ^a   Alder, Roger W ^b   Foxman, Bruce M ^a   Yang, Lin ^a  

^a BRANDEIS UNIVERSITY   (United States)

^b UNIVERSITY OF BRISTOL   (United Kingdom)

Author keywords

Azine; Calculation of pK a; Crisscross cycloaddition; Dipolar cycloaddition

Indexed keywords

AZINES; CRISSCROSS CYCLOADDITION; DIASTEREOMERS; DIPOLAR CYCLOADDITION;

CYCLOADDITION; METHYLATION; MOLECULAR SIEVES; MOLECULAR STRUCTURE; REDUCTION;

AMINES;

CITRONELLAL AZINE; DIAMINE; HYDRAZINE; SPARTEINE; TERPENOID; TERTIARY AMINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CYCLOADDITION; METHYLATION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 33847664656     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/V06-084     Document Type: Article

References (49)

1. For reviews of crisscross cycloadditions, see: (a) R. Grashley. In 1,3-Dipolar cycloaddition chemistry. Vol. 1. Edited by A. Padwa. John Wiley and Sons, New York. 1984. pp. 757-763;
2. (b) S. Rádl. Aldrichimica Acta, 30, 97 (1997).
3. (a) S.S. Mathur and H. Suschitzky. J. Chem. Soc. Perkin Trans, 1, 2479 (1975);
4. (b) K. Burger, H. Schickaneder, F. Hein, A. Gieren, V. Lamm, and H. Engelhardt. Liebigs Ann. Chem. 845 (1982);
5. (c) T. Shimizu, Y. Hayashi, M. Miki, and K. Teramura. J. Org. Chem. 52, 2277 (1987);
6. (d) M. Potáček, R. Marek, Z. Žák, J. Trottier, Z. Janoušek, and H. Viehe. Tetrahedron Lett. 34, 8341 (1993);
7. (e) M.G. Barlow, R.G. Pritchard, N.S. Suliman, and A.E. Tripping. Acta Crystalogr. Sect. C, 50, 553 (1994);
8. (f) M.M. Abdul-Ghani and A.E. Tipping. J. Fluorine Chem. 73, 203 (1995);
9. (g) G. Maas and V. Gettwert. Tetrahedron, 56, 4139 (2000);
10. (h) É. Frank, J. Wölfing, B. Aukszi, V. König, T. Schneider, and G. Schneider. Tetrahedron, 58, 6843 (2002);
11. (i) A.P. Molchanov, D.I. Sipkin, Yu. B. Koptelov, J. Kopf, and R.R. Kostikov. Russ. J. Org. Chem. 40, 67 (2004).
12. (a) A. Berkessel, M. Schröder, C.A. Sklorz, S. Tabanella, N. Vogl, J. Lex, and J.M. Neudörfl. J. Org. Chem. 69, 3050 (2004);
13. (b) J.-C. Kizirian, N. Cabello, L. Pinchard, J.-C. Caille, and A. Alexakis. Tetrahedron, 61, 8939 (2005).
14. (a) D. Hoppe and T. Hense. Angew. Chem. Int. Ed. Engl. 36, 2282 (1997);
15. (b) P.-W. Phuan, J.C. Ianni, and M.C. Kozlowski. J. Am. Chem. Soc. 126, 15473 (2004).
16. B. Fouchet, M. Joucla, and J. Hamelin. Tetrahedron Lett. 22, 1333 (1981).
17. S. Kobayashi, H. Shimizu, Y. Yamashita, H. Ishitani, and J. Kobayashi. J. Am. Chem. Soc. 124, 13678 (2002).
18. J. Elguero, R. Jacquier, and C. Marzin. Bull. Soc. Chim. Fr. 1374 (1969).
19. S.F. Nelsen, D.T. Rumack, L.W. Sieck, and M. Meot-Ner (Mautner). J. Am. Chem. Soc. 110, 6303 (1988).
20. (a) H. Stetter and H. Spangenberger. Chem. Ber. 91, 1982 (1958);
21. (b) F.J. Weigert. J. Org. Chem. 43, 622 (1978);
22. (c) S.F. Nelsen and M.R. Willi. J. Org. Chem. 49, 1 (1984);
23. (d) F. Alonso, G. Radivoy, and M. Yus. Tetrahedron, 56, 8673 (2000).
24. (a) J.M. Mellor and N.M. Smith. J. Chem. Soc. Perkin Trans. 1, 2927 (1984);
25. (b) S.E. Denmark, O. Nicaise, and J.P. Edwards. J. Org. Chem. 55, 6219 (1990).
26. S.F. Nelsen, J.T. Ippoliti, and P.A. Petillo. J. Org. Chem. 55, 3825 (1990).
27. S.H. Pine and B.L. Sanchez. J. Org. Chem. 36, 829 (1971).
28. Y. Chen, S.-K. Tian, and L. Deng. J. Am. Chem. Soc. 122, 9542 (2000).
29. (a) M. Asami, T. Suga, K. Honda, and S. Inoue. Tetrahedron Lett. 38, 6425 (1997);
30. (b) P. O'Brien. J. Chem. Soc. Perkin Trans, 1, 1439 (1998).
31. R.W. Alder, P. Eastment, N.M. Hext, R.E. Moss, A.G. Orpen, and J.M. White. J. Chem. Soc. Chem. Commun. 1528 (1988).
32. G.R. Weisman, M.E. Rogers, E.H. Wong, J.P. Jasinski, and E.S. Paight. J. Am. Chem. Soc. 112, 8604 (1990).
33. (a) I. Kaljurand, A. Kütt, L. Sooväli, T. Rodima, V. Mäemets, I. Lieto, and I.A Koppel. J. Org. Chem. 70, 1019 (2005);
34. (b) R. Schwesinger, H. Schlemper, C. Hasenfratz, J. Willaredt, T. Dambacher, T. Breuer, C. Ottaway, M. Fletschinger, J. Boele, H. Fritz, D. Putzas, H.W. Rotter, F.G. Bordwell, A.V. Satish, G.-Z. Ji, E.-M. Peters, K. Peters, H.G. von Schnering, and L. Walz. Liebigs Ann. 1055 (1996).
35. M.D. Liptak and G.C. Shields. J. Am. Chem. Soc. 123, 7314 (2001).
36. A.M. Magill, K.J. Cavell, and B.F. Yates. J. Am. Chem. Soc. 126, 8717 (2004).
37. A.M. Magill and B.F. Yates. Aust. J. Chem. 57, 1205 (2004).
38. R.W. Alder. J. Am. Chem. Soc. 127, 7924 (2005).
39. Schrödinger, LLC. Jaguar. Version 6.0 [computer program]. Schrödinger, LLC, New York. 2005.
40. A.D. Becke. J. Chem. Phys. 98, 5648 (1993).
41. C. Lee W. Yang, and R.G. Parr. Phys. Rev. B, 37, 785 (1988).
42. R.W. Alder, P.S. Bowman, W.R.S. Steele, and D.R. Winterman. J. Chem. Soc. Chem. Commun. 723 (1968).
43. A. Mucci, R. Domain, and R.L. Benoit. Can. J. Chem. 58, 953 (1980).
44. R.L. Benoit, D. Lefebvre, and M. Fréchette. Can. J. Chem. 65, 996 (1987).
45. A.F. Pozharskii, O.V. Ryabtsova, V.A. Ozeryanskii, A.V. Degtyarev, O.N. Kazheva, G.G. Alexandrov, and O.A. Dyachenko. J. Org. Chem. 68, 10109 (2003).
46. G. Chang, W.C. Guida, and W.C. Still. J. Am. Chem. Soc. 111, 4379 (1989).
47. M. Sauders, K.N. Houk, Y.D. Wu, W.C. Still, M. Lipton, G. Chang, and W.C. Guida. J. Am. Chem. Soc. 112, 1419 (1990).
48. F. Mohamadi, N.G.J. Richards, W.C. Guida, R. Liskamp, M. Lipton, G. Caulfield, G. Chang, T. Hendrickson, and W.C. Still. J. Comput. Chem. 11, 440 (1990).
49. Schrödinger, LLC. MacroModel. Version 9.0 [computer program]. Schrödinger, LLC, New York. 2005.