Five- and six-membered ring formation from the intramolecular reaction of a protonated oxirane and alkene

Tetrahedron

Volumn 64, Issue 40, 2008, Pages 9654-9661

  Coxon, James M ^a   Townsend, Michael A E ^a  

^a UNIVERSITY OF CANTERBURY   (New Zealand)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ETHYLENE OXIDE;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; PRIORITY JOURNAL; PROTON TRANSPORT;

EID: 49349106185     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.06.109     Document Type: Article

References (32)

1. Abe I., Rohmer M., and Prestwich G.D. Chem. Rev. 93 (1993) 2189
2. Wendt K.U., Schulz G.E., Corey E.J., and Liu D.R. Angew. Chem., Int. Ed. 39 (2000) 2812
3. Yoder R.A., and Johnston J.N. Chem. Rev. 105 (2005) 4730
4. Corey E.J., Cheng H., Baker C.H., Matsuda S.P.T., Li D., and Song X. J. Am. Chem. Soc. 119 (1997) 1277
5. Corey E.J., Cheng H., Baker C.H., Matsuda S.P.T., Li D., and Song X. J. Am. Chem. Soc. 119 (1997) 1289
6. Gao D., Pan Y.-K., Byun K., and Gao J. J. Am. Chem. Soc. 120 (1998) 4045
7. Corey E.J., and Staas D.D. J. Am. Chem. Soc. 120 (1998) 3526
8. Hess Jr. B.A. Collect. Czech. Chem. Commun. 68 (2003) 202
9. Baldwin J.E. J. Chem. Soc., Chem. Commun. (1976) 734
10. Frisch M.J., Trucks G.W., Schlegel H.B., Gill P.M.W., Johnson B.G., Robb M.A., Cheeseman J.R., Keith T., Petersson G.A., Montgomery J.A., Raghavachari K., Al-Laham M.A., Zakrzewski V.G., Ortiz J.V., Foresman J.B., Cioslowski J., Stefanov B.B., Nanayakkara A., Challacombe M., Peng C.Y., Ayala P.Y., Chen W., Wong M.W., Andres J.L., Replogle E.S., Gomperts R., Martin R.L., Fox D.J., Binkley J.S., Defrees D.J., Baker J., Stewart J.P., Head-Gordon M., Gonzalez C., and Pople J.A. Gaussian 94, Revision E.1 (1995), Gaussian, Pittsburgh, PA
11. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montgomery Jr. J.A., Vreven T., Kudin K.N., Burant J.C., Millam J.M., Iyengar S.S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G.A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J.E., Hratchian H.P., Cross J.B., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Ayala P.Y., Morokuma K., Voth G.A., Salvador P., Dannenberg J.J., Zakrzewski V.G., Dapprich S., Daniels A.D., Strain M.C., Farkas O., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Ortiz J.V., Cui Q., Baboul A.G., Clifford S., Cioslowski J., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Gonzalez C., and Pople J.A. Gaussian 03, Revision B.04 (2003), Gaussian, Pittsburgh, PA
12. Coxon J.M., Maclagan R.G.A.R., Rauk A., Thorpe A.J., and Whalen D. J. Am. Chem. Soc. 119 (1997) 4712
13. Smith M.B., and March J. March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. 5th ed. (2001), John Wiley and Sons, New York, NY, USA
14. Rauk A., Sorensen T.S., Maerker C., Carneiro J.W.d.M., Sieber S., and Schleyer P.v.R. J. Am. Chem. Soc. 118 (1996) 3761
15. Rauk A., Sorensen T.S., and Schleyer P.v.R. J. Chem. Soc., Perkin Trans. 2 (2001) 869
16. Kirchen R.P., Ranganayakulu K., and Sorensen T.S. J. Am. Chem. Soc. 109 (1987) 7811
17. Mesić M., Novak I., Sunko D.E., and Vančik H. J. Chem. Soc., Perkin Trans. 2 (1998) 2371
18. Abraham R.J., and Ribeiro D.S. J. Chem. Soc., Perkin Trans. 2 (2001) 302
19. Wiberg K.B., Hammer J.D., Castejon H., Bailey W.F., DeLeon E.L., and Jarret R.M. J. Org. Chem. 64 (1999) 2085
20. Freeman F., Kasner M.L., and Hehre W.J. THEOCHEM 574 (2001) 19
21. Jones Weldon A., Vickrey T.L., and Tschumper G.S. J. Phys. Chem. A 109 (2005) 11073
22. Stork G., and Cohen J.F. J. Am. Chem. Soc. 96 (1974) 5270
23. Coxon J.M., Hartshorn M.P., and Swallow W.H. Aust. J. Chem. 26 (1973) 2521
24. Na J., Houk K.N., Shevlin C.G., Janda K.D., and Lerner R.A. J. Am. Chem. Soc. 115 (1993) 8453
25. Coxon J.M., and Thorpe A.J. J. Org. Chem. 64 (1999) 5530
26. Coxon J.M., Morokuma K., Thorpe A.J., and Whalen D. J. Org. Chem. 63 (1998) 3875
27. For examples see:
28. Andrey O., Ducry L., Landais Y., Planchenault D., and Weber V. Tetrahedron 53 (1997) 4339
29. Bedford S.B., Bell K.E., Fenton G., Hayes C.J., Knight D.W., and Shaw D. Tetrahedron Lett. 33 (1992) 6511
30. Landais Y., and Planchenault D. Synlett (1995) 1191
31. Johnson C.D. Acc. Chem. Res. 26 (1993) 476
32. Coxon J.M., and Townsend M.A.E. Tetrahedron (2007) 5665