Stannylation/Destannylation. New Syntheses of Carbonyl Compounds via Organotin Intermediates

Journal of the American Chemical Society

Volumn 99, Issue 14, 1977, Pages 4836-4838

  Still, W Clark ^a  

^a VANDERBILT UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000451523     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00456a057     Document Type: Article

References (34)

1. E. J. Corey and R. H. Wollenberg, J. Am. Chem. Soc., 96, 5581 (1974);
2. J. Org. Chem., 40, 2265, 3788 (1975);
3. E. J. Corey, P. Ulrich, and J. M. Fitzpatrick, J. Am. Chem. Soc., 98, 222 (1976).
4. A. J. Bloodworth and A. G. Davies, Chem. Ind. (London), 490 (1972);
5. P. J. Smith, Smith, Chem. Ind. (London)., 1025 (1976).
6. J.-C. Lahournere and J. Valade, J. Organomet. Chem., 33, C7 (1971).
7. Stannyl cuprate addition: J. Hudec, J. Chem. Soc., Perkin Trans 1, 1020 (1975).
8. W. C. Still, J. Org. Chem., 41, 3061 (1976).
9. H. Gilman and S. D. Rosenberg, J. Am. Chem. Soc., 75, 2507 (1953);
10. D. Blake, G. E. Coates, and J. M. Tate, J. Chem. Soc., 618 (1961);
11. W. L. Wells and T. L. Brown, J. Organomet. Chem., 11, 271 (1968);
12. C. Tam-borski, F. E. Ford, and E. J. Soloski, J. Org. Chem., 28, 237 (1963);
13. H. Gilman, F. K. Cartledge, and S.-Y. Sim, J. Organomet. Chem., 1, 8 (1963);
14. A. T. Weibel and J. P. Oliver, J. Organomet. Chem., 82, 281 (1974).
15. C. H. W. Jones, R. G. Jones, P. Parington, and R. M. G. Roberts, J. Organomet. Chem., 32, 201 (1971).
16. All new compounds gave satisfactory IR, NMR, and C, H analyses.
17. R. K. Boeckman and S. M. Silver, J. Org. Chem., 40, 1755 (1975).
18. G. S. Koermer, M. L. Hall, and T. G. Traylor, J. Am. Chem. Soc., 94, 7205 (1972).
19. Cf. J. W. Patterson, Jr., and J. H. Fried, J. Org. Chem., 39, 2506 (1974);
20. E. S. Binkley and C. H. Heathcock, J. Org. Chem., 40, 2156 (1975).
21. C. Deblandre, M. Gielen, and J. Nasielski, Bull. Soc. Chim. Belg., 73, 214 (1964).
22. R. Ratcliffe and R. Rodehorst, J. Org. Chem., 35, 4000 (1970).
23. W. Pritzkow and H. Schaefer, Chem. Ber., 93, 2151 (1960);
24. V. Franzen and S. Otto, Chem. Ber., 94, 1360 (1961);
25. H. J. Bestmann and O. Kratzer, Chem. Ber., 96, 1899 (1963);
26. D. M. Lemal and A. J. Fry, Tetrahedron Lett., 775 (1961);
27. B. Ganem and R. K. Boeckman, Tetrahedron Lett., 719 (1974);
28. K. Baum, C. D. Beard, and V. Grakauskas, J. Am. Chem. Soc., 97, 267 (1975).
29. B. M. Trost, and J. L. Stanton, J. Am. Chem. Soc., 97, 4018 (1975);
30. B. M. Trost, K. Hiroi, and N. Holy, J. Am. Chem. Soc., 97, 5873 (1975);
31. W. Oppolzer, T. Sarkar, and K. K. Mahalanabis, Heiv. Chim. Acta, 59, 2012 (1976).
32. H. Hundsdiecker, Chem. Ber., 75, 460 (1942).
33. T.-L. Ho, Synth. Commun., 4, 265 (1974).
34. Address correspondence to Department of Chemistry, Columbia University, New York, N. Y. 10027.