New synthesis of 2-methyleneaziridines and 2-methyleneazetidines by dimethyl titanocene mediated methylenation of α- and β-lactams

Tetrahedron Letters

Volumn 41, Issue 12, 2000, Pages 1975-1978

  Abbaspour Tehrani, Kourosch ^a   De Kimpe, Norbert ^a  

^a GHENT UNIVERSITY   (Belgium)

Author keywords

Azetidines; Aziridines; Olefination

Indexed keywords

AZIRIDINE DERIVATIVE; BETA LACTAM; LACTAM; TITANIUM;

ARTICLE; CHEMICAL BINDING; CHEMICAL REACTION KINETICS; METAL BINDING; ORGANIC CHEMISTRY; REACTION ANALYSIS; SYNTHESIS;

EID: 0141962499     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00076-9     Document Type: Article

References (27)

1. (a) Del'tsova, D. P.; Gambaryan, N. P. Izv. Akad. Nauk. SSSR, Ser. Khim. 1976, 858-862; Chem. Abstr. 1976, 85, 123732.
2. (a) Del'tsova, D. P.; Gambaryan, N. P. Izv. Akad. Nauk. SSSR, Ser. Khim. 1976, 858-862; Chem. Abstr. 1976, 85, 123732.
3. (b) Zeifman, Y. V.; Ter-Gabrielyan, E. G.; Simonyan, L. A.; Gambaryan, N. P.; Knunyants, I. L. Izv. Akad. Nauk. SSSR, Ser. Khim. 1976, 1813-1817; Chem. Abstr. 1977, 86, 16466.
4. (b) Zeifman, Y. V.; Ter-Gabrielyan, E. G.; Simonyan, L. A.; Gambaryan, N. P.; Knunyants, I. L. Izv. Akad. Nauk. SSSR, Ser. Khim. 1976, 1813-1817; Chem. Abstr. 1977, 86, 16466.
5. (a) Wasserman, H. H.; Lipshutz, B. H.; Tremper, A. W.; Wu, J. S. J. Org. Chem. 1981, 46, 2991-2999.
6. (b) Wasserman, H. H.; Lipshutz, B. H.; Wu, J. S. Heterocycles 1977, 7, 321-326.
7. © Raap, R. Can. J. Chem. 1971, 49, 1792-1798.
8. (a) Pifferi, G.; Consonni, P.; Testa, E. Ann. Chim. (Rome) 1968, 58, 1283-1293; Chem. Abstr. 1969, 70, 68015.
9. (a) Pifferi, G.; Consonni, P.; Testa, E. Ann. Chim. (Rome) 1968, 58, 1283-1293; Chem. Abstr. 1969, 70, 68015.
10. (b) Pifferi, G.; Vigevani, A.; Consonni, P. Ann. Chim. (Rome) 1969, 59, 658-670; Chem. Abstr. 1970, 72, 90159.
11. (b) Pifferi, G.; Vigevani, A.; Consonni, P. Ann. Chim. (Rome) 1969, 59, 658-670; Chem. Abstr. 1970, 72, 90159.
12. Danion-Bougot, R.; Danion, D.; Carrié, R. Tetrahedron 1985, 41, 1953-1958.
13. Baldwin, J. E.; Edwards, A. J.; Farthing, C. N.; Russell, A. T. Synlett 1993, 49-50.
14. Sulmon, P.; De Kimpe, N.; Schamp, N. J. Org. Chem. 1988, 53, 4462-4465.
15. For a leading reference on the preparation and chemistry of methyleneaziridines, see: De Kimpe, N.; De Smaele, D.; Sakonyi, Z. J. Org. Chem. 1997, 62, 2448-2452.
16. (a) Ince, J.; Shipman, M.; Ennis, D. S. Tetrahedron Lett. 1997, 38, 5887-5890.
17. (b) Shipman, M.; Ross, T. R.; Slawin, A. M. Z. Tetrahedron Lett. 1999, 40, 6091-6092.
18. Petasis, N. A.; Bzowej, E. I. J. Am. Chem. Soc. 1990, 112, 6392-6394.
19. Petasis, N. A.; Akritopoulou, I. Synlett 1992, 665-667.
20. Petasis, N. A.; Lu, S.-P. Tetrahedron Lett. 1995, 36, 2393-2396.
21. Payack, J. F.; Hughes, D. L.; Cai, D.; Cottrel, I. F.; Verhoeven, T. R. Org. Prep. Proced. Int. 1995, 27, 707-709.
22. (a) Mori, M.; Chiba, K.; Okita, M.; Kayo, I.; Ban, Y. Tetrahedron 1985, 41, 375-385.
23. (b) Bartholomew, D.; Stocks, M. J. Tetrahedron Lett. 1991, 32, 4795-4798.
24. The spectrometric data of compound 5a are identical with those reported in Ref. 6.
25. +, 80); 206/208 (13); 192 (7); 181 (6); 180 (10); 179 (13); 178 (9); 172 (6); 170 (7); 166 (11); 154 (17); 153 (14); 152 (27); 151 (34); 142 (14); 139/141 (100); 138 (23); 127 (9); 111/113 (23); 75 (18); 66 (15); 65 (6); 51 (11); 44 (12); 41 (13); 40 (70).
26. Sheehan, J. C.; Beeson, J. H. J. Am. Chem. Soc. 1967, 89, 362-366.
27. +, 5); 152 (6); 124 (2); 112 (7); 111 (11); 110 (19); 108 (1); 98 (1); 96 (44); 95 (3); 94 (4); 93 (2); 83 (5); 82 (5); 81 (3); 80 (2); 79 (3); 71 (7); 70 (35); 69 (100); 68 (8); 67 (4); 58 (8); 57 (81); 56 (10); 55 (31); 54 (9); 53 (6); 43 (9); 42 (29); 41 (69). Bp 24-26°C/1.3 mmHg.