Anomalous products from intramolecular insertion reactions of rhodium carbenoids into the α-C-H bonds of ethers

Journal of Organic Chemistry

Volumn 62, Issue 15, 1997, Pages 4910-4911

  Clark, J Stephen ^a   Dossetter, Alexander G ^a   Russell, C Adam ^b   Whittingham, William G ^b  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

^b JEALOTT S HILL RESEARCH STATION   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; CYCLOPENTANONE DERIVATIVE; ETHER; FURANONE DERIVATIVE; RHODIUM; TETRAHYDROFURAN;

ARTICLE; CATALYSIS; CYCLIZATION; DATA ANALYSIS; GAS CHROMATOGRAPHY; HYDROGEN BOND; SPECTROSCOPY; STEREOCHEMISTRY;

EID: 0030753039     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970842p     Document Type: Article

References (24)

1. For the first examples of intramolecular C-H insertion of metal carbenoids to give cyclopentanones, see: (a) Wenkert, E.; Davis, L. L.; Mylari, B. L.; Solomon, M. F.; da Silva, R. R.; Shulman, S.; Warnet, R. J.; Ceccherelli, P.; Curini, M.; Pellicciari, R. J. Org. Chem. 1982, 47, 3242. (b) Taber, D. F.; Petty, E. H. J. Org. Chem. 1982, 47, 4808.
2. For the first examples of intramolecular C-H insertion of metal carbenoids to give cyclopentanones, see: (a) Wenkert, E.; Davis, L. L.; Mylari, B. L.; Solomon, M. F.; da Silva, R. R.; Shulman, S.; Warnet, R. J.; Ceccherelli, P.; Curini, M.; Pellicciari, R. J. Org. Chem. 1982, 47, 3242. (b) Taber, D. F.; Petty, E. H. J. Org. Chem. 1982, 47, 4808.
3. For reviews concerning the C-H insertion reactions of metal carbenoids, see: (a) Taber, D. F. In Comprehensive Organic Synthesis; Pattenden, G., Ed.; Pergamon Press: Oxford, 1991; Vol. 3, Chapter 4.2, p 1045. (b) Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091. (c) Doyle, M. P. In Comprehensive Organometallic Chemistry II; Hegedus, L. S., Ed.; Pergamon Press: New York, 1995; Vol. 12, Chapter 5.2, p 421.
4. For reviews concerning the C-H insertion reactions of metal carbenoids, see: (a) Taber, D. F. In Comprehensive Organic Synthesis; Pattenden, G., Ed.; Pergamon Press: Oxford, 1991; Vol. 3, Chapter 4.2, p 1045. (b) Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091. (c) Doyle, M. P. In Comprehensive Organometallic Chemistry II; Hegedus, L. S., Ed.; Pergamon Press: New York, 1995; Vol. 12, Chapter 5.2, p 421.
5. For reviews concerning the C-H insertion reactions of metal carbenoids, see: (a) Taber, D. F. In Comprehensive Organic Synthesis; Pattenden, G., Ed.; Pergamon Press: Oxford, 1991; Vol. 3, Chapter 4.2, p 1045. (b) Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091. (c) Doyle, M. P. In Comprehensive Organometallic Chemistry II; Hegedus, L. S., Ed.; Pergamon Press: New York, 1995; Vol. 12, Chapter 5.2, p 421.
6. Doyle, M. P. Aldrichim. Acta 1996, 29, 3 and references therein.
7. (a) McCarthy, N.; McKervey, M. A.; Ye, T.; McCann, M.; Murphy, E.; Doyle, M. P. Tetrahedron Lett. 1992, 33, 5983.
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9. (c) Watanabe, N.; Ohtake, Y.; Hashimoto, S.; Shiro, M.; Ikegami, S. Tetrahedron Lett. 1995, 36, 1491.
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11. Taber, D. F.; Song. Y. J. Org. Chem. 1996, 61, 6706.
12. Lee, E.; Choi, I.; Song, S. Y. J. Chem. Soc., Chem. Commun. 1995, 321.
13. Clark, J. S.; Dossetter, A. G.; Whittingham, W. G. Tetrahedron Lett. 1996, 37, 5605.
14. Ceccherelli, P.; Curini, M.; Marcotullio, M. C.; Rosati, O. Tetrahedron 1992, 48, 9767.
15. 4].
16. 4].
17. 4].
18. 4].
19. Russell, C. A. Unpublished results.
20. (a) Taber, D. F.; Ruckle, R. E., Jr. J. Am. Chem. Soc. 1986, 108, 7686.
21. (b) Doyle, M. P.; Westrum, L. J.; Wolthuis, W. N. E.; See, M. M.; Boone, W. P.; Bagheri, V.; Pearson, M. M. J. Am. Chem. Soc. 1993, 115, 958.
22. (c) Pirrung, M. C.; Morehead, A. T., Jr. J. Am. Chem. Soc. 1994, 116, 8991.
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24. Hydride transfer has been proposed to account for the formation of other anomalous products during C-H insertion reactions of rhodium carbenoids: Doyle, M. P.; Dyatkin, A. B.; Autry, C. L. J. Chem. Soc., Perkin Trans. 1 1996, 619.