An Alternative Route for Carboni-Lindsey Reaction: N,N Cycloaddition of an Alkene to s-Tetrazine

Organic Letters

Volumn 3, Issue 11, 2001, Pages 1725-1727

  Zhou, Xiaojian ^a   Kovalev, Efim G ^a   Klug, Jacob T ^a   Khodorkovsky, Vladimir ^a  

^a BEN GURION UNIVERSITY OF THE NEGEV   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0038765391     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol015918p     Document Type: Article

References (13)

1. Carboni, R. A.; Lindsey, R. V. J. Am. Chem. Soc. 1959, 81, 4342.
2. Sauer, J. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon Press: Oxford, 1996; Vol. 6, p 901.
3. (b) Sauer, J.; Heldmann, D. K.; Hetzenegger, J.; Krauthan, J.; Sichert, H.; Schuster, J. Eur. J. Org. Chem. 1998, 2885.
4. (c) Boger, D. L. Chem. Rev. 1986, 86, 781.
5. Calculations were performed on the B3LYP/6-31(d) level using Jaguar 3.5 software, Schroedinger, Inc., Portland, Oregon, 1998.
6. Abdel-Rahman, M. O.; Kira, M. A.; Tolba, M. N. Tetrahedron Lett. 1968, 35, 3871.
7. Gibson, H. W.; Bailey, F. C. Tetrahedron 1974, 30, 2050.
8. (a) Kovalev, E. G.; Rusinov, G. L.; Anufriev, V. A.; Egorova, L. G. Khim. Geterosikl. Soedin. 1990, 1038.
9. (b) Kovalev, E. G.; Rusinov, G. L.; Aleksandrov, G. G.; Anufriev, V. A.; Sidorov, E. O.; Chernyshev, A. I. Khim. Geterosikl. Soedin. 1991, 1545.
10. 6 TMS) δ 46.42, 111.14, 125.71, 127.59, 128.46, 128.62, 133.42, 143.90, 149.52, 151.54.
11. 6, TMS) δ 46.71, 120.86, 125.84, 127.39, 128.64, 134.49, 144.97, 148.27, 158.15, 164.82. X-ray structure experiment will be published elsewhere.
12. int = 0.0342). Structure was refined to R1 = 0.0566, wR2 = 0.1648, GOF = 1.058, 496 parameters. The hydrogen atoms were included with geometrically calculated positions and refined using riding model. Bruker SHELX software package was used for all calculations and drawings. Atomic coordinates, bond lengths and angles, and anisotropic parameters have been deposited at the Cambridge Crystallographic Data Center. The authors are thankful to Dr. A. Ellern for the X-ray experiment.
13. Lang, S. A., Jr.; Ziegler, C. B., Jr. In Progress in Heterocyclic Chemistry; Suschitzky, H., Scriven, E. F. V., Eds.; Pergamon Press: Oxford, 1990; Vol. 2, p 108.