Homolytic displacements at carbon centres. Part 1. Reaction of allyl- and allenyl-cobaloximes with polyhalogenomethanes

Journal of the Chemical Society, Perkin Transactions 2

Volumn , Issue 8, 1979, Pages 1050-1057

  Bury, Adrian ^a   Cooksey, Christopher J ^a   Funabiki, Takuso ^a   Gupta, B Dass ^a   Johnson, Michael D ^a  

^a UNIVERSITY COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 37049108019     PISSN: 1472779X     EISSN: None     Source Type: Journal    
DOI: 10.1039/P29790001050     Document Type: Article

References (23)

1. Preliminary report, B. D. Gupta, T. Funabiki, and M. D. Johnson, J. Amer. Chem. Soc., 1976, 98, 6697.
2. C. J. Cooksey, D. Dodd, M. D. Johnson, and B. L. Lockman, J.C.S. Dalton, 1979, 1814.
3. K. U. Ingold and B. P. Roberts, ‘Homolytic Substitution Reactions,’ Wiley-Interscience, New York, 1970.
4. M. L. Poutsma, in ‘Free Radicals,’ ed. J. K. Kochi, Wiley-Interscience, New York, 1973, vol. II, pp. 142-149.
5. J. Grignon, C. Servens, and M. Pereyre, J. Organometallic Chem., 1975, 96, 225.
6. R. A. Jackson and M. Townson, Tetrahedron Letters, 1973, 193.
7. J. H. Incremona and C. J. Upton, J. Amer. Chem. Soc., 1972, 94, 301.
8. The dicinnamyls were identified by comparison with authentic materials prepared as a mixture from cinnamyl chloride and magnesium, H. P. Koch, J. Chem. Soc., 1948, 1111.
9. A. A. Kamyshova, E. T. Chukovskaya, and R. K. Friedlina, Izvest. Akad. Nauk. S.S.S.R. Ser. Khim., 1973, 2004.
10. R. K. Friedlina, R. D. Ismailov, and B. A. Englin, Izvest. Akad. Nauk. S.S.S.R. Ser Khim., 1972, 2320.
11. M. S. Kharasch and M. Sage, J. Org. Chem., 1949, 14, 79.
12. CoII(dmgH)2B abstracts halogen atoms from a variety of alkyl halides. The reaction with bromotrichloromethane is particularly fast, J. Halpern and P. F. Phelan, J. Amer. Chem. Soc., 1972, 94, 1881.
13. J. H. Espenson, personal communication.
14. A. Rockenbauer, E. Budo-Zahonyi, and L. I. Simandi, J.C.S. Dalton, 1975, 1729.
15. G. N. Schrauzer, A. Ribeiro, L. P. Lee, and R. K. Y. Ho, Angew. Chem. Internat. Edn., 1971, 10, 807.
16. G. N. Schrauzer, Inorg. Synth., 1968, 11, 61.
17. C. Bied-Charreton and A. Gaudemer, J. Orgnometallic Chem., 1977, 124, 299.
18. W. H. Pailes and H. P. C. Hogenkamp, Biochemistry, 1968, 7, 4160.
19. D. Dodd and M. D. Johnson, J. Organometallic Chem., 1973, 52, 1.
20. J. Halpern, M. S. Chan, J. Hanson, T. S. Roche, and J. A. Topich, J. Amer. Chem. Soc., 1975, 97, 1606.
21. G. F. Hennion and A. P. Boisselle, J. Org. Chem., 1961, 26, 725.
22. C. J. Cooksey, D. Dodd, C. Gatford, M. D. Johnson, G. J. Lewis, and D. M. Titchmarsh, J.C.S. Perkin II, 1972, 655.
23. T. P. Collman, T. N. Cawse, and J. W. Kay, Inorg. Chem., 1969, 8, 2574.