Tetrahydrofuran as an one-electron donor: Highly diastereoselective coupling of cobalt-complexed propargyl alcohol

Journal of Organometallic Chemistry

Volumn 544, Issue 1, 1997, Pages 143-145

  Melikyan, Gagik G ^a   Deravakian, Asatour ^a  

^a CALIFORNIA STATE UNIVERSITY   (United States)

Author keywords

Diastereoselectivity; Propargyl cation; Propargyl radical; Reductive dimerization; Single electron transfer

Indexed keywords

EID: 0031554992     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(97)00286-6     Document Type: Article

References (24)

1. [1] (a) G.G. Melikyan, V.M. Mkrtchyan, K.A. Atanesyan, G.Kh. Asaryan, Sh.O. Badanyan, Bioorg. Khim. 16 (1990) 1000; C.A. 113(25) 230995j;
2. [1] (a) G.G. Melikyan, V.M. Mkrtchyan, K.A. Atanesyan, G.Kh. Asaryan, Sh.O. Badanyan, Bioorg. Khim. 16 (1990) 1000; C.A. 113(25) 230995j;
3. (b) G.G. Melikyan, A. Mineif, O. Vostrowsky, H.J. Bestmann, Synthesis (1991) 633;
4. (c) G.G. Melikyan, O. Vostrowsky, W. Bauer, H.J. Bestmann, J. Organometal. Chem. 423 (1992) C24.
5. [2] H.H. Freedman, in: G.A. Olah, P.R. Schleyer (Eds.), Carbonium Ions, vol.4, Wiley, NY, 1973, p. 1501.
6. [3] K.M. Nicholas, Acc. Chem. Res. 20 (1987) 207.
7. [4] Alternative scenario includes a one-electron oxidation of C-H bond by cation 1, and subsequent dimerization of propargyl radical 4.
8. [5] Mono-cluster (3,4-diphenyl-1,5-hexadiyne)dicobalt hexacarbonyl (10) is also formed as a minor product.
9. [6] C. Ruchardt, Top. Curr. Chem. 88 (1980) 1; K.H. Eichin, K.J. McCullough, H.D. Beckhaus, C. Ruchardt, Angew. Chem., Int. Ed. Engl. 17 (1978) 934 and references therein.
10. [6] C. Ruchardt, Top. Curr. Chem. 88 (1980) 1; K.H. Eichin, K.J. McCullough, H.D. Beckhaus, C. Ruchardt, Angew. Chem., Int. Ed. Engl. 17 (1978) 934 and references therein.
11. [7] N.A. Porter, P.J. Krebs, in: E.L. Eliel, S.H. Wilen (Eds.), Topics in Stereochemistry 18 (1988) 97.
12. [8] L.A. Paquette, I. Itoh, K.B. Lipkowitz, J. Org. Chem. 41 (1976) 3524.
13. 3: (a) J.E. Mahler, D.H. Gibson, R. Pettit, J. Am. Chem. Soc. 85 (1963) 3959;
14. (b) A.J. Pearson, Y. Chen, M.L. Daroux, A.A. Tanaka, M. Zettler, J. Chem. Soc. Chem. Comm. (1987) 155.
15. 4: N. Berre-Cosquer, R. Kergoat P. L'Haridon, Organometallics 11 (1992) 721.
16. 3: S. Top, G. Jaouen, J. Organomet. Chem. 336 (1987) 143.
17. [12] In some cases the stereoselectivity of dimerization has not been reported; (a) ferrocenylcarbinols: M. Cais, A. Eisenstadt, J. Org. Chem. 30 (1965) 1148;
18. 6: W.E. Geiger, T. Genneth, G.A. Lane, Organometallics 5 (1986) 1352;
19. 6: S. Padmanabhan, K.M. Nicholas, J. Organomet. Chem. 212 (1981) 115.
20. [13] G.G. Melikyan, R.C. Combs, J. Lamírand, M. Khan, K.M. Nicholas, Tetrahedron Lett. (1994) 363.
21. [14] R.D. Cannon, Electron Transfer Reactions, Butterworths, London, 1980.
22. [15] Electron transfer in inorganic, organic and biological systems, in: J.R. Bolton, N. Mataga, G. McLendon, Advances in Chemistry, Series 228, ACS, Washington, 1991.
23. [16] A remote analogy is represented by a spontaneous dimerization of ferrocenylmethanol in the presence of sulfuric acid: K.L. Rinehart, C.J. Michejda, P.A. Kittle, J. Am. Chem. Soc. 81 (1959) 3162.
24. For one-step hydrogenolysis see Refs. (1a) and P.L. Pauson, W.E. Watts, J. Chem. Soc. (1962) 3880.