Generation and 1,3-dipolar cycloadditions of azomethine ylides derived from difluorocarbene and imines

Tetrahedron Letters

Volumn 38, Issue 23, 1997, Pages 4187-4190

  Novikov, Mikhail S ^a   Khlebnikov, Alexander F ^a   Masalev, Alexander E ^a   Kostikov, Rafael R ^a  

^a ST PETERSBURG STATE UNIVERSITY   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

FLUORINE; IMINE; PYRROLIDINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM;

EID: 0031006833     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00872-1     Document Type: Article

References (20)

1. Padwa, A. Ed:1,3-Dipolar cycloaddition chemistry: Wiley-Interscience: New York, 1984, Vols. I and II.
2. Khlebnikov, A. F.; Novikov, M. S.; Kostikov, R. R. Adv Heterocycl. Chem. 1996, 65, 93-233.
3. Khlebnikov, A. F.; Novikov, M. S.; Kostikov, R. R. Khim. Geterocycl. Soedin. 1987, N10, 1336-1342; Chem. Heterocycl. Comp. 1987, N10, 1070-1076.
4. Khlebnikov, A. F.; Novikov, M. S.; Kostikov, R. R. Khim. Geterocycl. Soedin. 1987, N10, 1336-1342; Chem. Heterocycl. Comp. 1987, N10, 1070-1076.
5. Novikov, M. S.; Khlebnikov, A. F.; Kostikov, R. R. Zh. Org. Khim. 1988, 24, 1917-1922; J. Org. Chem. USSR 1988, 24, 1728-1732.
6. Novikov, M. S.; Khlebnikov, A. F.; Kostikov, R. R. Zh. Org. Khim. 1988, 24, 1917-1922; J. Org. Chem. USSR 1988, 24, 1728-1732.
7. Khlebnikov, A. F.; Novikov, M. S.; Kostikov, R. R. Zh. Org. Khim. 1990, 26, 1899-1903; J. Org. Chem. USSR 1990, 26, 1642-1645.
8. Khlebnikov, A. F.; Novikov, M. S.; Kostikov, R. R. Zh. Org. Khim. 1990, 26, 1899-1903; J. Org. Chem. USSR 1990, 26, 1642-1645.
9. Novikov, M. S.; Khlebnikov, A. F.; Kostikov, R. R. Zh. Org. Khim. 1996, 32, 667-674.
10. Khlebnikov, A. F.; Nikiforova, T. Yu.; Kostikov, R. R. Zh. Org. Khim. 1996, 32, 746-760.
11. Khlebnikov, A. F.; Kostik, E. I.; Kostikov, R. R.; Bespalov, V. Y. Khim. Geterocycl. Soedin. 1990, N3, 355-362; Chem. Heterocycl. Comp. 1990, N3, 304-311.
12. Khlebnikov, A. F.; Kostik, E. I.; Kostikov, R. R.; Bespalov, V. Y. Khim. Geterocycl. Soedin. 1990, N3, 355-362; Chem. Heterocycl. Comp. 1990, N3, 304-311.
13. Khlebnikov, A. F.; Kostik, E. I.; Kostikov, R. R. Synthesis 1993, 568-570.
14. Fluorine-containing azomethine ylides have only once been mentioned (McCarthy, J. R.; Barney, C. L.; O'Donnell, J.; Huffman, J. C. J. Chem. Soc. Chem. Commun. 1987, 469-470) as assumed intermediates in formation of ethyl 1-difluoromethyl-3,3-diphenylaziridine-2-carboxylate.
15. Fritz, H. P.; Kornrumpf, W. Z. Z. Naturforsch. 1981, 36b, 1375-1380.
16. 3) δ 169.3, 168.6, 168.4, 168.4, 134.6, 129.2, 128.9, 127.3, 61.6, 53.1, 52.3, 51.9, 48.2, 46.7, 42.5; MS (70 eV) m/z (%) 349 (15), 318 (6), 290 (22), 276 (10), 258 (39), 244 (100), 230 (38), 216 (38), 198 (25), 118 (72), 116 (17), 115 (62), 113 (47), 91 (89).
17. 2Me gives signals at 3.7-3.8 ppm.
18. The deshielding effect of the cis-phenyl group shifts the methine protons in compounds (1b-3b) low-field (4.20-4.48 ppm) with respect to the corresponding signals in (1a-3a) (3.85-3.89 ppm).
19. 1H NOESY experiment with compounds (1b, 3b) points to a strong interaction between 4-H and 5-H and a weak interaction between 3-H and 4-H, while in the case of compound (4b) there is a strong interaction of 4-H with both 5-H and 3-H.
20. Tsuge, O.; Ueno, K.; Kanemasa, S.; Yorozu, K. Bull. Chem. Soc. Jpn. 1986, 59, 1809-1824.