Synthesis of 1,1-bis(trimethylstannyl)cyclopropanes by the SRN1 mechanism

Organometallics

Volumn 28, Issue 8, 2009, Pages 2646-2649

  Guastavino, Javier F ^a   Rossi, Roberto A ^a  

^a DEPARTAMENTO DE FISICOQUÍMICA   (Argentina)

Author keywords

[No Author keywords available]

Indexed keywords

DICHLOROCARBENE; PHOTO-INDUCED;

OLEFINS;

PROPANE;

EID: 65649146431     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om801104e     Document Type: Article

References (17)

1. For a review of the synthesis and applications of cyclopropylstan- nanes, see: Rubina, M.; Gevorgyan, V. Tetrahedron 2004, 60, 3129, and references therein.
2. As far as we know there is only one report of the synthesis of their 1,1-analogues, such as 7,7-bis(trimethylstannyl)norcarane; see: Seyferth, D.; Lambert, R. L., Jr. J. Organomet. Chem. 1975, 88, 287.
3. For reviews, see: (a) Rossi, R. A.; Pierini, A. B.; Penenory, A. B. Chem. Rev. 2003, 103, 71-167.
4. b) Rossi, R. A.; Pierini, A. B.; Santiago, A. N. In Organic Reactions; Paquette, L. A., Bittman, R., Eds.; Wiley & Sons: New York, 1999; pp 1-271.
5. c) Rossi, R. A. In Synthetic Organic Photochemistry; Griesberck, A. G., Mattay, J., Eds.; Marcel Dekker: New York, 2005; Vol.12, Chapter 15, pp 495-527.
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10. Bardagi, J. I.; Rossi, R. A. J. Org. Chem. 2008, 73, 4491.
11. Santiago, A. N.; Stahl, A. E.; Rodriguez, G. L.; Rossi, R. A. J. Org. Chem. 1997, 62, 4406.
12. Santiago, A. N.; Toledo, C. A.; Rossi, R. A. J. Org. Chem. 2002, 67, 2494.
13. For reviews on the preparation and synthetic applications of dihalogenocyclopropanes, see: (a) Halton, B.; Harvey. J. Synlett 2006, 1975.
14. b) Banwell, M. G.; Beck, D. A. S.; Stanislawski, P. C.; Sydnes, M. O.; Taylor, R. M. Curr. Org. Chem. 2005, 9, 1589.
15. Fedorynski, M. Chem. Rev. 2003, 103, 1099, and references therein.
16. It has been demonstrated before that when the halogen-metal exchange is faster than the SRN1 mechanism, the anion formed is protonated very rapidly by liquid ammonia; see ref 5a.
17. Mitchell, T. N.; El-Behairy, M. J. Organomet. Chem. 1979, 172, 293.