A thermal reductive-elimination route to perbutylated cyclopolystannanes

Organometallics

Volumn 15, Issue 13, 1996, Pages 2849-2851

  Xi, Rimo ^a   Babcock, Jason R ^a   Sita, Lawrence R ^a  

^a UNIVERSITY OF CHICAGO   (United States)

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[No Author keywords available]

Indexed keywords

EID: 5344281174     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om960289m     Document Type: Article

References (22)

1. Jousseaume, B.; Noiret, N.; Pereyre, M.; Saux, A. Organometallics 1994, 13, 1034.
2. Depending on reaction conditions, these methods have been shown to provide varying ratios of 1 to 2 in the range of 90/10 to 30/ 70.
3. (a) Jousseaume, B.; Gouron, V.; Maillard, B.; Pereyre, M.; Francés, J.-M. Organometallics 1990, 9, 1330.
4. (b) Jousseaume, B.; Noiret, N.; Pereyre, M.; Frances, J.-M.; Pétraud, M. Organometallics 1992, 11, 3910.
5. Neumann, W. P.; Schneider, B. Angew. Chem., Int. Ed. Engl. 1964, 3, 751.
6. 119Sn NMR spectroscopy that 1 and 2 are the sole cyclopolystannane products that are formed at room temperature by this route, together with a number of additional coproducts containing the Sn-H functionality.
7. (a) Davidson, I. M. T.; Jones, M. R.; Pett, C. J. Chem. Soc. B 1967, 937.
8. (b) Kauffmann, T.; Kriegesmann, R.; Hamsen, A. Chem. Ber. 1982, 115, 1818.
9. Sita, L. R.; Terry, K. W.; Shibata, K. J. Am. Chem. Soc. 1995, 117, 8049.
10. Sita, L. R. Organometallics 1992, 12, 1442.
11. 2Sn: C, 50.69; H, 9.19. Found: C, 50.25; H, 9.61.
12. 28OSn: C, 46.94; H, 9.19. Found: C, 47.27; H, 9.60.
13. 1 In addition, a pure sample of 2 was obtained by preparative reverse-phase HPLC (acetonitrile/ dichloromethane gradient).
14. 119Sn NMR spectra of the initially obtained thermolysis product.
15. 1 this thermal stability of 1 and 2 is in stark contrast to that displayed by dodecamethylcyclohexastannane; see: Watta, B.; Neumann, W. P.; Sauer, J. Organometallics 1985, 4, 1954.
16. 36OSn: C, 52.92; H, 9.99. Found: C, 52.98; H, 10.27.
17. Similar product mixtures are obtained from the radical initiated monohydrostannation of norbornadiene with trialkylstannanes; see: (a) Kuivila, H. G. Acc. Chem. Res. 1968, 1, 299. (b) Peterson, D. J.; Robbing, M. D.; Hansen, J. R. J. Organomet. Chem. 1974, 73, 237.
18. Similar product mixtures are obtained from the radical initiated monohydrostannation of norbornadiene with trialkylstannanes; see: (a) Kuivila, H. G. Acc. Chem. Res. 1968, 1, 299. (b) Peterson, D. J.; Robbing, M. D.; Hansen, J. R. J. Organomet. Chem. 1974, 73, 237.
19. 2MH(OMe) (M = Ge and Sn); see ref 4 and: Massol, M.; Satgé, J.; Riviére, P.; Barrau, J. J. Organomet. Chem. 1970, 22, 599.
20. Neumann, W. P. The Organic Chemistry of Tin; Wiley: New York, 1970.
21. For instance, attempts to trap 12 with 2,3-dimethylbutadiene led only to a complex mixture of hydrostannated products resulting from trapping of the intermediate 9.
22. Cyclopolystannanes formally possess Sn(II) centers.