Nonstereospecific 1,3-dipolar cycloadditions - LUMO(dipole)-HOMO(dipolarophile) controlled reactions

Tetrahedron Letters

Volumn 39, Issue 8, 1998, Pages 807-810

  Weber, Andreas ^a   Sauer, Jürgen ^a  

^a UNIVERSITY OF REGENSBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; AMPHOLYTE; ENAMINE; THIOCARBONYL YLIDE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NONHUMAN;

EID: 0032546105     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10762-6     Document Type: Article

References (17)

1. 1. Huisgen, R. 1,3-Dipolar Cycloadditions - Introduction, Survey, Mechanism. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; John Wiley: New York, 1984, pp. 35-42.
2. 2. Dorn, H.; Ozegowski, R.; Gründemann, E. J. Prakt. Chem. 1979, 321, 555-564.
3. 3. Huisgen, R.; Weinberger, R. Tetrahedron Lett. 1985, 26, 5119-5122. Dorn, H. Tetrahedron Lett. 1985, 26, 5123-5126.
4. 3. Huisgen, R.; Weinberger, R. Tetrahedron Lett. 1985, 26, 5119-5122. Dorn, H. Tetrahedron Lett. 1985, 26, 5123-5126.
5. 4. Huisgen, R. Steric Course and Mechanism of 1,3-Dipolar Cycloadditions. In Advances in Cycloaddition, Vol 1; JAI Press: New York, 1988, pp. 1-31.
6. 5. Huisgen, R.; Mloston, G.; Langhals, E. J. Am. Chem. Soc. 1986, 108, 6401-6402.
7. 6. Huisgen, R.; Langhals, E.; Nöth, H. Tetrahedron Lett. 1986, 27, 5475-5478.
8. 7. Huisgen, R.; Mloston, G.; Langhals, E. J. Org. Chem. 1986, 51, 4085-4087.
9. 8. Riebel, P.; Weber, A.; Troll, T.; Sauer, J.; Breu, J. Tetrahedron Lett. 1996, 37, 1583-1586.
10. 9. Riebel, P.; Weber, A.; Troll, T.; Sauer, J.; Breu, J.; Nöth, H. Tetrahedron Lett. 1996, 37, 1587-1590.
11. 10. Breu, J.; Range, K. J.; Riebel, P.; Weber, A.; Sauer, J. Acta Crystallogr. Sect. C 1996, 52, 2053-2056.
12. 5 (451.6): C, 77.13; H, 7.37; N, 15.51. Found: C, 76.92; H, 7.49; N, 15.34.
13. 12. Breu, J.; Range, K. J.; Weber, A.; Sauer, J. Acta Crystallogr. Sect. C, submitted.
14. 4o (452.6): C, 76.96; H, 7.13; N, 12.38. Found: C, 76.92; H, 7.25; N, 12.32.
15. 14. Weber, A. 1,3-Dipolare Cycloadditionen stabiler Azomethinylide. Präparative und mechanistische Untersuchungen, PhD-thesis Universität Regensburg, 1997.
16. 15. In order to measure the reaction rate solutions of 6 and 7 were treated with a large excess of cyclooctyne, a highly reactive 2π-compound, which rapidly traps the dipole 5 irreversibly.
17. 16. Sauer, J.; Prahl, H. Chem. Ber. 1969, 102, 1917-1927.