Carbenes in polycyclic systems. Generation and fate of pentacyclo[5.4.0.02,6.03,10.55,9] undecanylidene species

Tetrahedron Letters

Volumn 43, Issue 42, 2002, Pages 7573-7575

  Veljković, Jelena ^a   Klaić, Lada ^a   Mlinarić Majerski, Kata ^a  

^a RUDER BO KOVI INSTITUTE   (Croatia)

Author keywords

Azoalkane; Cage compounds; Carbene; Dicarbene

Indexed keywords

ALKANE DERIVATIVE; AZOALKANE; CARBENOID; CHEMICAL COMPOUND; HYDRAZONE DERIVATIVE; LITHIUM; SODIUM; TRIDEC 4 ENE; UNCLASSIFIED DRUG; UNDECA 2,6 DIENE; UNDECANYLIDENE;

ARTICLE; CHEMICAL PARAMETERS; CHEMICAL PROCEDURES; PYROLYSIS;

EID: 0037078414     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01761-6     Document Type: Article

References (31)

1. Regitz, M. Carbene(oide), Carbine, Parts 1 and 2. In Methoden der Organischen Chemie; Houben-Weyl, Ed; Thieme: Stuttgart, 1989; Vol. E19b. Wentrup, C. Reactive Molecules; John Wiley and Sons: New York, 1984; Chapter 4.
2. Jones M. Jr., Moss R.A. Reactive Intermediates. 3:1985;John Wiley and Sons, New York.
3. Majerski Z., Kostov V., Hibšer M., Mlinarić-Majerski K. Tetrahedron Lett. 31:1990;915-916.
4. Majerski Z., Žuanić M. J. Am. Chem. Soc. 109:1987;3496-3498.
5. Hamon D.P.G., Trenerry V.C. J. Am. Chem. Soc. 103:1981;4962-4965.
6. Mlinarić-Majerski K., Šafar Cvitaš D., Veljković J. J. Org. Chem. 59:1994;2374-2380.
7. Mlinarić-Majerski K., Šafar Cvitaš D., Majerski Z. Tetrahedron Lett. 32:1991;1655-1658.
8. Mlinarić-Majerski K., Majerski Z. J. Am. Chem. Soc. 105:1983;7389-7395.
9. Mlinarić-Majerski K., Majerski Z. J. Am. Chem. Soc. 102:1980;1418-1419.
10. Majerski Z., Veljković J., Kaselj M. J. Org. Chem. 53:1988;2662-2664.
11. Jones M. Jr. Brinker U.H., Advances in Carbene Chemistry. 2:1998;77-97 JAI Press, Stamford.
12. Borden W.T. Synlett. 1996;711-719.
13. Hrovat D.A., Borden W.T. J. Am. Chem. Soc. 114:1992;2719-2720.
14. Mlinarić-Majerski K., Veljković J., Kaselj M. Croat. Chem. Acta. 73:2000;575-584.
15. Marchand A.P., Kumar K.A., Mlinarić-Majerski K., Veljković J. Tetrahedron. 54:1988;15105-15112.
16. 3a
17. + 512.154651, found 512.154284.
18. Marchand A.P., Allen R.W. J. Org. Chem. 39:1974;1596-1596.
19. Eaton P.E., Cassar L., Hudson R.A., Hwang D.R. J. Org. Chem. 41:1976;1445-1448.
20. Underwood G.R., Ramamoorthy B. Tetrahedron Lett. 1970;4125-4127.
21. + 172.099499, found 172.099938.
22. Engel P.S. Chem. Rev. 80:1980;99-150. and references cited therein.
23. Patai S. The Chemistry of the Hydrazo, Azo, and Azoxy Groups. 1975;Wiley, New York.
24. For extrusion of nitrogen from some substituted cage azoalkanes see: Marchand A.P., Reddy G.M., Watson W.H., Kashyap R.P., Nagl A. J. Org. Chem. 56:1991;277-282.
25. Turro N.J., Liu K.C., Cherry W., Liu J.M., Jacobson B.M. Tetrahedron Lett. 1978;555-558.
26. Allred E.L., Beck B.R. Tetrahedron Lett. 1974;437-440.
27. Berson J.A., Davis R.F. J. Am. Chem. Soc. 94:1972;3658-3659.
28. McNeil D.W., Kent M.E., Hedaya E., D'Angelo P.F., Schissel P.O. J. Am. Chem. Soc. 93:1971;3817-3818.
29. For the chemistry of 2,3-diazabicyclo[2.2.2]octene and other DBO derivatives see: (a) Engel, P. S.; Horsey, D. W.; Keys, D. E.; Nalepa, C. J.; Soltero, L. R. J. Am. Chem. Soc. 1983, 105, 7108-7114; (b) Engel, P. S.; Nalepa, C. J.; Horsey, D. W.; Keys, D. E.; Grow, R. T. J. Am. Chem. Soc. 1983, 105, 7102-7107 and references cited therein.
30. For the chemistry of 2,3-diazabicyclo[2.2.2]octene and other DBO derivatives see: (a) Engel, P. S.; Horsey, D. W.; Keys, D. E.; Nalepa, C. J.; Soltero, L. R. J. Am. Chem. Soc. 1983, 105, 7108-7114; (b) Engel, P. S.; Nalepa, C. J.; Horsey, D. W.; Keys, D. E.; Grow, R. T. J. Am. Chem. Soc. 1983, 105, 7102-7107 and references cited therein.
31. A benzene solution of azoalkane 2 was irradiated for 4 h at room temperature through a Pyrex filter with a 450 W mercury lamp. A solution of 2 in methanol was irradiated in a Ryonet reactor equipped with 350 nm lamps (16×24 W).