Mn(III)-based oxidative free-radical cyclizations of unsaturated ketones

Journal of Organic Chemistry

Volumn 61, Issue 22, 1996, Pages 7832-7847

  McCarthy Cole, Bridget ^a   Han, Luning ^a   Snider, Barry B ^a  

^a BRANDEIS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0343513998     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961199u     Document Type: Article

References (48)

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2. For reviews see: (a) Snider, B. B. Chem. Rev. 1996, 96, 339. (b) Iqbal, J.; Bhatia, B.; Nayyar, N. K. Chem. Rev. 1994, 94, 519. (c) Melikyan, G. G. Synthesis 1993, 833. (d) Badanyan, Sh. O.; Melikyan, G.G.; Mkrtchyan, D. A. Russ. Chem. Rev. 1989, 58, 286; Uspekhi Khim. 1989, 58, 475. (e) de Klein, W. J. In Organic Synthesis by Oxidation with Metal Compounds; Mijs, W. J., de Jonge, C. R. H., Eds.; Plenum Press: New York, 1986; pp 261-314.
3. For reviews see: (a) Snider, B. B. Chem. Rev. 1996, 96, 339. (b) Iqbal, J.; Bhatia, B.; Nayyar, N. K. Chem. Rev. 1994, 94, 519. (c) Melikyan, G. G. Synthesis 1993, 833. (d) Badanyan, Sh. O.; Melikyan, G.G.; Mkrtchyan, D. A. Russ. Chem. Rev. 1989, 58, 286; Uspekhi Khim. 1989, 58, 475. (e) de Klein, W. J. In Organic Synthesis by Oxidation with Metal Compounds; Mijs, W. J., de Jonge, C. R. H., Eds.; Plenum Press: New York, 1986; pp 261-314.
4. For reviews see: (a) Snider, B. B. Chem. Rev. 1996, 96, 339. (b) Iqbal, J.; Bhatia, B.; Nayyar, N. K. Chem. Rev. 1994, 94, 519. (c) Melikyan, G. G. Synthesis 1993, 833. (d) Badanyan, Sh. O.; Melikyan, G.G.; Mkrtchyan, D. A. Russ. Chem. Rev. 1989, 58, 286; Uspekhi Khim. 1989, 58, 475. (e) de Klein, W. J. In Organic Synthesis by Oxidation with Metal Compounds; Mijs, W. J., de Jonge, C. R. H., Eds.; Plenum Press: New York, 1986; pp 261-314.
5. For reviews see: (a) Snider, B. B. Chem. Rev. 1996, 96, 339. (b) Iqbal, J.; Bhatia, B.; Nayyar, N. K. Chem. Rev. 1994, 94, 519. (c) Melikyan, G. G. Synthesis 1993, 833. (d) Badanyan, Sh. O.; Melikyan, G.G.; Mkrtchyan, D. A. Russ. Chem. Rev. 1989, 58, 286; Uspekhi Khim. 1989, 58, 475. (e) de Klein, W. J. In Organic Synthesis by Oxidation with Metal Compounds; Mijs, W. J., de Jonge, C. R. H., Eds.; Plenum Press: New York, 1986; pp 261-314.
6. For reviews see: (a) Snider, B. B. Chem. Rev. 1996, 96, 339. (b) Iqbal, J.; Bhatia, B.; Nayyar, N. K. Chem. Rev. 1994, 94, 519. (c) Melikyan, G. G. Synthesis 1993, 833. (d) Badanyan, Sh. O.; Melikyan, G.G.; Mkrtchyan, D. A. Russ. Chem. Rev. 1989, 58, 286; Uspekhi Khim. 1989, 58, 475. (e) de Klein, W. J. In Organic Synthesis by Oxidation with Metal Compounds; Mijs, W. J., de Jonge, C. R. H., Eds.; Plenum Press: New York, 1986; pp 261-314.
7. For preliminary communications on portions of this work see: (a) Snider, B. B.; McCarthy Cole, B. J. Org. Chem. 1995, 60, 5376. (b) Snider, B. B.; McCarthy, B. A. In Benign by Design. Alternative Chemical Synthesis for Pollution Prevention; Anastas, P., Farris, C., Eds.; ACS Symposium Series; American Chemical Society: Washington, DC, 1994; Chapter 7.
8. For preliminary communications on portions of this work see: (a) Snider, B. B.; McCarthy Cole, B. J. Org. Chem. 1995, 60, 5376. (b) Snider, B. B.; McCarthy, B. A. In Benign by Design. Alternative Chemical Synthesis for Pollution Prevention; Anastas, P., Farris, C., Eds.; ACS Symposium Series; American Chemical Society: Washington, DC, 1994; Chapter 7.
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35. The observed coupling constants are similar to those observed for related 4-acetoxy-2-cyclohexenones: Widmer, E.; Zell, R.; Lukac, T.; Casadei, M.; Schonholzer, P.; Broger, E. A. Helv. Chim. Acta 1981, 64, 2405.
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46. r1 = 344/5.65 = 60.8 so that cyclization of a 5-hexenyl radical is about 60 times faster than cyclization of a 4-phenylbutyl radical.
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