Preparation and diazodecomposition reaction of an α-diazocarbonyl-tethered tricarbonyl(η4-cyclohexadiene)iron complex

Journal of Organic Chemistry

Volumn 61, Issue 13, 1996, Pages 4188-4189

  Petrel, Trevor A ^a   Stephan, Jennifer M ^a   McDaniel, Keith F ^a   McMills, Mark C ^a   Rheingold, Arnold L ^b   Yap, Glenn P A ^b  

^a OHIO UNIVERSITY   (United States)

^b UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0242326332     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960229q     Document Type: Article

References (16)

1. See, for example: Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, U.K., 1994; Vol. 12, Chapters 6.1, 6.3, 8.2, and 9.1.
2. See, for example: Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, U.K., 1994; Vol. 12, Chapters 5.1 and 5.2.
3. 3
4. 3
5. 4-cycloheptatriene)iron has been reported to provide the cyclopropanation product as is shown below. See: (a) Goldschmidt, Z.; Antebi, S.; Goldberg, I. J. Organomet. Chem. 1984, 260, 105. (b) See also: Taylor, G. A. J. Chem. Soc., Perkin Trans. 1 1979, 1716. (Matrix Presented)
6. 4-cycloheptatriene)iron has been reported to provide the cyclopropanation product as is shown below. See: (a) Goldschmidt, Z.; Antebi, S.; Goldberg, I. J. Organomet. Chem. 1984, 260, 105. (b) See also: Taylor, G. A. J. Chem. Soc., Perkin Trans. 1 1979, 1716. (Matrix Presented)
7. Franck-Neumann and co-workers recently have recently reported the preparation and reactions of several tricarbonyl iron π-complexes bearing a free diazo group. See: Franck-Neumann, M.; Geoffroy, P.; Winling, A. Tetrahedron Lett. 1995, 36, 8213.
8. For a recent review of this chemistry see: Pearson, A. J. Iron Compounds in Organic Synthesis; Academic Press: San Diego, 1994; Chapter 5.
9. Davies, H. M. L.; Cantrell, W. R.; Romines, K. R.; Baum, J. S. Org. Synth. 1991, 70, 93.
10. The iron complex resulting from the reaction of acetone with iron cation 1 provides a good comparison for these compounds. The 5-endo hydrogen in this complex comes at 2.4 ppm. See: Birch, A. J.; Chamberlain, K. B.; Haas, M. A.; Thompson, D. J. J. Chem. Soc., Perkin Trans. 1 1973, 1882. (Matrix Presented)
11. For specific examples of rhodium(II)-catalyzed diazodecomposition reactions leading to C-H insertion see: (a) Taber, D. F.; Petty, E. H.; Raman, K. J. Am. Chem. Soc. 1985, 107, 196. (b) Taber, D. F.; Ruckle, R. E., Jr. J. Am. Chem. Soc. 1986, 108, 7686. (c) 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.
12. For specific examples of rhodium(II)-catalyzed diazodecomposition reactions leading to C-H insertion see: (a) Taber, D. F.; Petty, E. H.; Raman, K. J. Am. Chem. Soc. 1985, 107, 196. (b) Taber, D. F.; Ruckle, R. E., Jr. J. Am. Chem. Soc. 1986, 108, 7686. (c) 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.
13. For specific examples of rhodium(II)-catalyzed diazodecomposition reactions leading to C-H insertion see: (a) Taber, D. F.; Petty, E. H.; Raman, K. J. Am. Chem. Soc. 1985, 107, 196. (b) Taber, D. F.; Ruckle, R. E., Jr. J. Am. Chem. Soc. 1986, 108, 7686. (c) 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.
14. 4-diene)iron complexes as protecting groups for 1,3-dienes see: Donaldson, W. A. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, U.K., 1994; Vol. 12, Chapter 6.2.
15. Intramolecular cyclopropanation of conjugated dienes has been demonstrated. See: Hudlicky, T. et al. Tetrahedron 1987, 43, 5685.
16. The author has deposited atomic coordinates for 4 with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.