New reductive deiodination reaction by hydrogen atom transfer from cyclohexane

Chemical Communications

Volumn , Issue 4, 1997, Pages 353-354

  Boivin, Jean ^a   Quiclet Sire, Béatrice ^b   Ramos, Laure ^a   Zard, Samir Z ^a,b  

^a LABORATOIRE DE SYNTHÈSE ORGANIQUE   (France)

^b CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002313573     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a607459f     Document Type: Article

References (22)

1. R. D. Chambers and S. R. James, in Comprehensive Organic Chemistry, ed. D. H. R. Barton and W. D. Ollis, Pergamon Press, Oxford, 1979, vol. 1, pp. 493-575.
2. S. Knapp, in Advances in Heterocyclic Natural Product Synthesis, ed. W. H. Pearson, JAI Press, Connecticut, 1996, pp. 57-98; K. E. Harding and T. H. Tiner, in Comprehensive Organic Synthesis, ed. B. M. Trost, I. Fleming and M. F. Semmelhack, Pergamon Press, Oxford, 1991, vol. 4, ch. 1.9, pp. 363-421; G. Cardillo and M. Orena, Tetrahedron, 1990, 46, 3321; M. D. Dowle and D. I. Davies, Chem. Soc. Rev., 1979, 171.
3. S. Knapp, in Advances in Heterocyclic Natural Product Synthesis, ed. W. H. Pearson, JAI Press, Connecticut, 1996, pp. 57-98; K. E. Harding and T. H. Tiner, in Comprehensive Organic Synthesis, ed. B. M. Trost, I. Fleming and M. F. Semmelhack, Pergamon Press, Oxford, 1991, vol. 4, ch. 1.9, pp. 363-421; G. Cardillo and M. Orena, Tetrahedron, 1990, 46, 3321; M. D. Dowle and D. I. Davies, Chem. Soc. Rev., 1979, 171.
4. S. Knapp, in Advances in Heterocyclic Natural Product Synthesis, ed. W. H. Pearson, JAI Press, Connecticut, 1996, pp. 57-98; K. E. Harding and T. H. Tiner, in Comprehensive Organic Synthesis, ed. B. M. Trost, I. Fleming and M. F. Semmelhack, Pergamon Press, Oxford, 1991, vol. 4, ch. 1.9, pp. 363-421; G. Cardillo and M. Orena, Tetrahedron, 1990, 46, 3321; M. D. Dowle and D. I. Davies, Chem. Soc. Rev., 1979, 171.
5. S. Knapp, in Advances in Heterocyclic Natural Product Synthesis, ed. W. H. Pearson, JAI Press, Connecticut, 1996, pp. 57-98; K. E. Harding and T. H. Tiner, in Comprehensive Organic Synthesis, ed. B. M. Trost, I. Fleming and M. F. Semmelhack, Pergamon Press, Oxford, 1991, vol. 4, ch. 1.9, pp. 363-421; G. Cardillo and M. Orena, Tetrahedron, 1990, 46, 3321; M. D. Dowle and D. I. Davies, Chem. Soc. Rev., 1979, 171.
6. M. Pereyre, J.-P. Quintard and A. Rahm, Tin in Organic Synthesis, Butterworths, London, 1987; W. P. Neumann, Synthesis, 1987, 665.
7. M. Pereyre, J.-P. Quintard and A. Rahm, Tin in Organic Synthesis, Butterworths, London, 1987; W. P. Neumann, Synthesis, 1987, 665.
8. T. Imamoto, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon Press, Oxford, 1991, vol. 8, pp. 793-809.
9. D. P. Curran, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon Press, Oxford, 1991; vol. 4, pp. 715-831. D. P. Curran, Synthesis, 1988, 417, 489.
10. D. P. Curran, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon Press, Oxford, 1991; vol. 4, pp. 715-831. D. P. Curran, Synthesis, 1988, 417, 489.
11. B. Quiclet-Sire and S. Z. Zard, J. Am. Chem. Soc., 1996, 118, 9190.
12. I. D. Jenkins, J. Chem. Soc., Chem. Commun., 1994, 1227; W. K. Busfield, I. D. Grice, I. D. Jenkins and M. J. Monteiro, J. Chem. Soc., Perkin Trans. 2, 1994, 1071; W. K. Busfield, I. D. Grice and I. D. Jenkins, J. Chem. Soc., Perkin Trans. 2, 1994, 1079; B. P. Roberts and A. J. Steel, J. Chem. Soc., Perkin Trans. 2, 1994, 2411; P. Kaushal, L. H. Mock and B. P. Roberts, J. Chem. Soc., Perkin Trans. 2, 1990, 1663 and references cited therein. For reviews on the polar effects in radical reactions, see J. M. Tedder, Angew. Chem., Int. Ed. Engl., 1982, 21, 401; Tetrahedron, 1982, 38, 313; G. A. Russell, in Free Radicals, ed. J. K. Kochi, Wiley, New York, 1973, vol. 1, ch. 7.
13. I. D. Jenkins, J. Chem. Soc., Chem. Commun., 1994, 1227; W. K. Busfield, I. D. Grice, I. D. Jenkins and M. J. Monteiro, J. Chem. Soc., Perkin Trans. 2, 1994, 1071; W. K. Busfield, I. D. Grice and I. D. Jenkins, J. Chem. Soc., Perkin Trans. 2, 1994, 1079; B. P. Roberts and A. J. Steel, J. Chem. Soc., Perkin Trans. 2, 1994, 2411; P. Kaushal, L. H. Mock and B. P. Roberts, J. Chem. Soc., Perkin Trans. 2, 1990, 1663 and references cited therein. For reviews on the polar effects in radical reactions, see J. M. Tedder, Angew. Chem., Int. Ed. Engl., 1982, 21, 401; Tetrahedron, 1982, 38, 313; G. A. Russell, in Free Radicals, ed. J. K. Kochi, Wiley, New York, 1973, vol. 1, ch. 7.
14. I. D. Jenkins, J. Chem. Soc., Chem. Commun., 1994, 1227; W. K. Busfield, I. D. Grice, I. D. Jenkins and M. J. Monteiro, J. Chem. Soc., Perkin Trans. 2, 1994, 1071; W. K. Busfield, I. D. Grice and I. D. Jenkins, J. Chem. Soc., Perkin Trans. 2, 1994, 1079; B. P. Roberts and A. J. Steel, J. Chem. Soc., Perkin Trans. 2, 1994, 2411; P. Kaushal, L. H. Mock and B. P. Roberts, J. Chem. Soc., Perkin Trans. 2, 1990, 1663 and references cited therein. For reviews on the polar effects in radical reactions, see J. M. Tedder, Angew. Chem., Int. Ed. Engl., 1982, 21, 401; Tetrahedron, 1982, 38, 313; G. A. Russell, in Free Radicals, ed. J. K. Kochi, Wiley, New York, 1973, vol. 1, ch. 7.
15. I. D. Jenkins, J. Chem. Soc., Chem. Commun., 1994, 1227; W. K. Busfield, I. D. Grice, I. D. Jenkins and M. J. Monteiro, J. Chem. Soc., Perkin Trans. 2, 1994, 1071; W. K. Busfield, I. D. Grice and I. D. Jenkins, J. Chem. Soc., Perkin Trans. 2, 1994, 1079; B. P. Roberts and A. J. Steel, J. Chem. Soc., Perkin Trans. 2, 1994, 2411; P. Kaushal, L. H. Mock and B. P. Roberts, J. Chem. Soc., Perkin Trans. 2, 1990, 1663 and references cited therein. For reviews on the polar effects in radical reactions, see J. M. Tedder, Angew. Chem., Int. Ed. Engl., 1982, 21, 401; Tetrahedron, 1982, 38, 313; G. A. Russell, in Free Radicals, ed. J. K. Kochi, Wiley, New York, 1973, vol. 1, ch. 7.
16. I. D. Jenkins, J. Chem. Soc., Chem. Commun., 1994, 1227; W. K. Busfield, I. D. Grice, I. D. Jenkins and M. J. Monteiro, J. Chem. Soc., Perkin Trans. 2, 1994, 1071; W. K. Busfield, I. D. Grice and I. D. Jenkins, J. Chem. Soc., Perkin Trans. 2, 1994, 1079; B. P. Roberts and A. J. Steel, J. Chem. Soc., Perkin Trans. 2, 1994, 2411; P. Kaushal, L. H. Mock and B. P. Roberts, J. Chem. Soc., Perkin Trans. 2, 1990, 1663 and references cited therein. For reviews on the polar effects in radical reactions, see J. M. Tedder, Angew. Chem., Int. Ed. Engl., 1982, 21, 401; Tetrahedron, 1982, 38, 313; G. A. Russell, in Free Radicals, ed. J. K. Kochi, Wiley, New York, 1973, vol. 1, ch. 7.
17. I. D. Jenkins, J. Chem. Soc., Chem. Commun., 1994, 1227; W. K. Busfield, I. D. Grice, I. D. Jenkins and M. J. Monteiro, J. Chem. Soc., Perkin Trans. 2, 1994, 1071; W. K. Busfield, I. D. Grice and I. D. Jenkins, J. Chem. Soc., Perkin Trans. 2, 1994, 1079; B. P. Roberts and A. J. Steel, J. Chem. Soc., Perkin Trans. 2, 1994, 2411; P. Kaushal, L. H. Mock and B. P. Roberts, J. Chem. Soc., Perkin Trans. 2, 1990, 1663 and references cited therein. For reviews on the polar effects in radical reactions, see J. M. Tedder, Angew. Chem., Int. Ed. Engl., 1982, 21, 401; Tetrahedron, 1982, 38, 313; G. A. Russell, in Free Radicals, ed. J. K. Kochi, Wiley, New York, 1973, vol. 1, ch. 7.
18. I. D. Jenkins, J. Chem. Soc., Chem. Commun., 1994, 1227; W. K. Busfield, I. D. Grice, I. D. Jenkins and M. J. Monteiro, J. Chem. Soc., Perkin Trans. 2, 1994, 1071; W. K. Busfield, I. D. Grice and I. D. Jenkins, J. Chem. Soc., Perkin Trans. 2, 1994, 1079; B. P. Roberts and A. J. Steel, J. Chem. Soc., Perkin Trans. 2, 1994, 2411; P. Kaushal, L. H. Mock and B. P. Roberts, J. Chem. Soc., Perkin Trans. 2, 1990, 1663 and references cited therein. For reviews on the polar effects in radical reactions, see J. M. Tedder, Angew. Chem., Int. Ed. Engl., 1982, 21, 401; Tetrahedron, 1982, 38, 313; G. A. Russell, in Free Radicals, ed. J. K. Kochi, Wiley, New York, 1973, vol. 1, ch. 7.
19. I. D. Jenkins, J. Chem. Soc., Chem. Commun., 1994, 1227; W. K. Busfield, I. D. Grice, I. D. Jenkins and M. J. Monteiro, J. Chem. Soc., Perkin Trans. 2, 1994, 1071; W. K. Busfield, I. D. Grice and I. D. Jenkins, J. Chem. Soc., Perkin Trans. 2, 1994, 1079; B. P. Roberts and A. J. Steel, J. Chem. Soc., Perkin Trans. 2, 1994, 2411; P. Kaushal, L. H. Mock and B. P. Roberts, J. Chem. Soc., Perkin Trans. 2, 1990, 1663 and references cited therein. For reviews on the polar effects in radical reactions, see J. M. Tedder, Angew. Chem., Int. Ed. Engl., 1982, 21, 401; Tetrahedron, 1982, 38, 313; G. A. Russell, in Free Radicals, ed. J. K. Kochi, Wiley, New York, 1973, vol. 1, ch. 7.
20. J. Thieme, H. Karl and J. Schwentener, Synthesis, 1978, 696.
21. D. Crich, A. L. J. Beckwith, C. Chen, Q. Yao, J. G. E. Davison, C. Anaya de Parrodi, L. Quintero-Cortes and J. Sandoval-Ramirez, J. Am. Chem. Soc., 1995, 117, 8575.
22. D. H. R. Barton, W. Hartwig and W. B. Motherwell, J. Chem. Soc., Chem. Commun., 1982, 447.