Chemically Induced Anion Radical Cycloadditions: Intramolecular Cyclobutanation of Bis(enones) via Homogeneous Electron Transfer

Journal of the American Chemical Society

Volumn 126, Issue 6, 2004, Pages 1634-1635

  Yang, Jingkui ^a   Felton, Greg A N ^a   Bauld, Nathan L ^a   Krische, Michael J ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANION; KETONE; RADICAL;

ARTICLE; CYCLOADDITION; CYCLOBUTANATION; DIELS ALDER REACTION; ELECTROCHEMISTRY; ELECTRON TRANSPORT; REACTION ANALYSIS; STEREOCHEMISTRY; STOICHIOMETRY;

EID: 1242269276     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja030543j     Document Type: Article

References (16)

1. Bauld, N. L. Tetrahedron 1989, 45, 5307.
2. Bauld, N. L. In Electron Transfer in Chemistry; Balzani, V., Ed.; Wiley-VCH: Weinheim, 2001; Vol. 2, p 133.
3. For electrochemically induced anion radical cyclobutanation, see: (a) Delaunay, J.; Mabon, G.; Orliac, A.; Simonet, J. Tetrahedron Lett. 1990. 31, 667.
4. (b) Jannsen, R.; Motevalli, M.; Utley, J. H. P. J. Chem. Soc., Chem. Commun. 1998, 539.
5. (c) Roh, Y.; Jang, H.-Y.; Lynch, V.; Bauld, N. L.; Krische, M. J. Org. Lett. 2002, 4, 611.
6. Anion radicals have been implicated as reactive intermediates in the Co-catalyzed [2 + 2] cycloaddition of bis(enones): (a) Baik, T.-G.; Wang, L.-C. ; Luiz, A.-L.; Krische, M. J. J. Am. Chem. Soc. 2001, 123, 6716.
7. (b) Wang, L.-C.; Jang, H.-.; Lynch, V.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 9448.
8. For other pericyclic reactions of anion radicals, see: (a) Bauld, N. L.; Chang, C.-S.; Farr, F. R. J. Am. Chem. Soc. 1972, 94, 7164.
9. (b) Bauld, N. L.; Cessac, J.; Chang, C.-S. Farr, F. F.; Holloway, R. J. Am. Chem. Soc. 1976, 98, 4561.
10. (c) Fox, M. A.; Hurst, J. R. J. Am. Chem. Soc. 1984, 106, 7626.
11. (d) Borhani, D. W.; Greene, F. D. J. Org. Chem. 1986, 51, 1563.
12. (e) Witmer, M.; Altmann, E.; Young, H.; Sancar, A.; Begley, T. P. J. Am. Chem. Soc. 1989, 111, 9264.
13. (f) Pasto, D. J.; Yang, S.-H. J. Org. Chem. 1989, 54, 3544.
14. β,β-Coupling of bis(enones) with and without subsequent aldolization has previously been observed under the conditions of electron transfer. For selected examples, see: (a) Enholm, E. J.; Kinter, K. S. J. Am. Chem. Soc. 1991, 113, 7784.
15. (b) Hays, D. S.; Fu, G. C. J. Org. Chem. 1996, 61, 4.
16. It appears unlikely that the aldol-type cyclization occurs at the stage of distonic anion radical in view of the fact that aldol type products are not formed in the electrochemical reactions, which also involve distonic anion radical intermediates.