TEMPO-induced generation of alkyl radicals from B-alkylcatecholboranes

Synlett

Volumn , Issue 6, 1999, Pages 807-809

  Ollivier, Cyril ^a   Chuard, Rachel ^a   Renaud, Philippe ^a  

^a UNIVERSITY OF FRIBOURG   (Switzerland)

Author keywords

Alkoxyamine; Alkyl radical; Alkyl catecholborane

Indexed keywords

ALKYL GROUP; BORANE DERIVATIVE; RADICAL; TEMPOL;

ARTICLE; CHEMICAL INTERACTION; CHEMICAL REACTION; CHEMICAL STRUCTURE; MOLECULAR DYNAMICS; PHYSICAL CHEMISTRY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0033036268     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2718     Document Type: Article

References (44)

1. Reviews on organoboranes: Brown, H. C. In Hydroboration, 2nd printing with Nobel Lecture; Benjamin-Cumming: Reading, 1980. Brown, H. C. In Boranes in Organic Chemistry, Cornell University Press: Ithaca, 1972. Brown, H. C.; Kramer, G. W.; Levy, A. B.; Midland, M. M. In Organic Synthesis via Boranes; Wiley: New York, 1975. Pelter, A.; Smith, K. In Comprehensive Organic Chemistry, Vol. 3; Barton, D. H. R., Ollis, W. D. Eds; Pergamon Press: Oxford, 1979, p 689. Brown H. C.; Smith, K. in Kirk-Othmer Encyclopaedia of Chemical Technology, 3rd ed. Vol. 12; Wiley: New York, 1980, p 793. Pelter, A.; Smith, K. and Brown H. C. In Borane Reagents; Academic Press: London, 1988. Matteson, D. S. Stereodirected Synthesis with Organoboranes; Springer: Berlin, 1995.
2. Reviews on organoboranes: Brown, H. C. In Hydroboration, 2nd printing with Nobel Lecture; Benjamin-Cumming: Reading, 1980. Brown, H. C. In Boranes in Organic Chemistry, Cornell University Press: Ithaca, 1972. Brown, H. C.; Kramer, G. W.; Levy, A. B.; Midland, M. M. In Organic Synthesis via Boranes; Wiley: New York, 1975. Pelter, A.; Smith, K. In Comprehensive Organic Chemistry, Vol. 3; Barton, D. H. R., Ollis, W. D. Eds; Pergamon Press: Oxford, 1979, p 689. Brown H. C.; Smith, K. in Kirk-Othmer Encyclopaedia of Chemical Technology, 3rd ed. Vol. 12; Wiley: New York, 1980, p 793. Pelter, A.; Smith, K. and Brown H. C. In Borane Reagents; Academic Press: London, 1988. Matteson, D. S. Stereodirected Synthesis with Organoboranes; Springer: Berlin, 1995.
3. Reviews on organoboranes: Brown, H. C. In Hydroboration, 2nd printing with Nobel Lecture; Benjamin-Cumming: Reading, 1980. Brown, H. C. In Boranes in Organic Chemistry, Cornell University Press: Ithaca, 1972. Brown, H. C.; Kramer, G. W.; Levy, A. B.; Midland, M. M. In Organic Synthesis via Boranes; Wiley: New York, 1975. Pelter, A.; Smith, K. In Comprehensive Organic Chemistry, Vol. 3; Barton, D. H. R., Ollis, W. D. Eds; Pergamon Press: Oxford, 1979, p 689. Brown H. C.; Smith, K. in Kirk-Othmer Encyclopaedia of Chemical Technology, 3rd ed. Vol. 12; Wiley: New York, 1980, p 793. Pelter, A.; Smith, K. and Brown H. C. In Borane Reagents; Academic Press: London, 1988. Matteson, D. S. Stereodirected Synthesis with Organoboranes; Springer: Berlin, 1995.
4. Reviews on organoboranes: Brown, H. C. In Hydroboration, 2nd printing with Nobel Lecture; Benjamin-Cumming: Reading, 1980. Brown, H. C. In Boranes in Organic Chemistry, Cornell University Press: Ithaca, 1972. Brown, H. C.; Kramer, G. W.; Levy, A. B.; Midland, M. M. In Organic Synthesis via Boranes; Wiley: New York, 1975. Pelter, A.; Smith, K. In Comprehensive Organic Chemistry, Vol. 3; Barton, D. H. R., Ollis, W. D. Eds; Pergamon Press: Oxford, 1979, p 689. Brown H. C.; Smith, K. in Kirk-Othmer Encyclopaedia of Chemical Technology, 3rd ed. Vol. 12; Wiley: New York, 1980, p 793. Pelter, A.; Smith, K. and Brown H. C. In Borane Reagents; Academic Press: London, 1988. Matteson, D. S. Stereodirected Synthesis with Organoboranes; Springer: Berlin, 1995.
5. Reviews on organoboranes: Brown, H. C. In Hydroboration, 2nd printing with Nobel Lecture; Benjamin-Cumming: Reading, 1980. Brown, H. C. In Boranes in Organic Chemistry, Cornell University Press: Ithaca, 1972. Brown, H. C.; Kramer, G. W.; Levy, A. B.; Midland, M. M. In Organic Synthesis via Boranes; Wiley: New York, 1975. Pelter, A.; Smith, K. In Comprehensive Organic Chemistry, Vol. 3; Barton, D. H. R., Ollis, W. D. Eds; Pergamon Press: Oxford, 1979, p 689. Brown H. C.; Smith, K. in Kirk-Othmer Encyclopaedia of Chemical Technology, 3rd ed. Vol. 12; Wiley: New York, 1980, p 793. Pelter, A.; Smith, K. and Brown H. C. In Borane Reagents; Academic Press: London, 1988. Matteson, D. S. Stereodirected Synthesis with Organoboranes; Springer: Berlin, 1995.
6. Reviews on organoboranes: Brown, H. C. In Hydroboration, 2nd printing with Nobel Lecture; Benjamin-Cumming: Reading, 1980. Brown, H. C. In Boranes in Organic Chemistry, Cornell University Press: Ithaca, 1972. Brown, H. C.; Kramer, G. W.; Levy, A. B.; Midland, M. M. In Organic Synthesis via Boranes; Wiley: New York, 1975. Pelter, A.; Smith, K. In Comprehensive Organic Chemistry, Vol. 3; Barton, D. H. R., Ollis, W. D. Eds; Pergamon Press: Oxford, 1979, p 689. Brown H. C.; Smith, K. in Kirk-Othmer Encyclopaedia of Chemical Technology, 3rd ed. Vol. 12; Wiley: New York, 1980, p 793. Pelter, A.; Smith, K. and Brown H. C. In Borane Reagents; Academic Press: London, 1988. Matteson, D. S. Stereodirected Synthesis with Organoboranes; Springer: Berlin, 1995.
7. Reviews on organoboranes: Brown, H. C. In Hydroboration, 2nd printing with Nobel Lecture; Benjamin-Cumming: Reading, 1980. Brown, H. C. In Boranes in Organic Chemistry, Cornell University Press: Ithaca, 1972. Brown, H. C.; Kramer, G. W.; Levy, A. B.; Midland, M. M. In Organic Synthesis via Boranes; Wiley: New York, 1975. Pelter, A.; Smith, K. In Comprehensive Organic Chemistry, Vol. 3; Barton, D. H. R., Ollis, W. D. Eds; Pergamon Press: Oxford, 1979, p 689. Brown H. C.; Smith, K. in Kirk-Othmer Encyclopaedia of Chemical Technology, 3rd ed. Vol. 12; Wiley: New York, 1980, p 793. Pelter, A.; Smith, K. and Brown H. C. In Borane Reagents; Academic Press: London, 1988. Matteson, D. S. Stereodirected Synthesis with Organoboranes; Springer: Berlin, 1995.
8. Brown, H. C.; Kabalka, G. W. J. Am. Chem. Soc. 1970, 92, 714. Brown, H. C.; Negishi, E. J. Am. Chem. Soc. 1971, 93, 3777.
9. Brown, H. C.; Kabalka, G. W. J. Am. Chem. Soc. 1970, 92, 714. Brown, H. C.; Negishi, E. J. Am. Chem. Soc. 1971, 93, 3777.
10. For review articles, see: Brown, H. C.; Midland, M. M. Angew. Chem. Int. Ed. Engl. 1972, 11, 692. Ghosez, A.; Giese, B.; Zipse, H. in Houben-Weyl, 4th ed., Vol. E19a; Regitz, M., Giese, B., Eds.; p 753.
11. For review articles, see: Brown, H. C.; Midland, M. M. Angew. Chem. Int. Ed. Engl. 1972, 11, 692. Ghosez, A.; Giese, B.; Zipse, H. in Houben-Weyl, 4th ed., Vol. E19a; Regitz, M., Giese, B., Eds.; p 753.
12. Nozaki, K.; Oshima, K.; Utimoto, K. J. Am. Chem. Soc. 1987, 109, 2547.
13. Formation of boron enolates from the reaction of enolate radicals with triethylborane has been reported: Nozaki, K.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1991, 64, 403.
14. Miura, K.; Ichinose, Y.; Nozaki, K.; Fugami, K.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1989, 62, 143.
15. Ollivier, C.; Renaud, P. Chem. Eur. J. 1999, 5, in press.
16. Recently, radical chain reactions involving alkylboranes and heteroatom centered radicals have been reported: N-centered radicals: Miyabe, H.; Ushiro, C.; Naito, T. Chem. Commun. 1997, 1789; Miyabe, H.; Shibata, R.; Ushiro, C.; Naito, T. Tetrahedron Lett. 1998, 39, 631; Bertrand, M. P.; Feray, L.; Nouguier, R.; Stella, L. Synlett 1998, 780; Miyabe, H.; Yoshioka, N.; Ueda, M.; Naito, T. J. Chem. Soc. Perkin Trans. 1 1998, 3659. O-centered radicals: Brown, H. C.; Midland, M. M. Angew. Chem. Int. Ed. Engl. 1972, 11, 692; Nozaki, K.; Oshima, K. Chem. Commun. 1998, 3659; Utimoto, K. Bull. Chem. Soc. Jpn. 1991, 64, 403; Clive, D. L. J.; Postema, M. H. D. J. Chem. Soc., Chem. Commun. 1993, 429; Devin, P.; Fensterbank, L.; Malacria, M. Tetrahedron Lett. 1998, 39, 833.
17. Recently, radical chain reactions involving alkylboranes and heteroatom centered radicals have been reported: N-centered radicals: Miyabe, H.; Ushiro, C.; Naito, T. Chem. Commun. 1997, 1789; Miyabe, H.; Shibata, R.; Ushiro, C.; Naito, T. Tetrahedron Lett. 1998, 39, 631; Bertrand, M. P.; Feray, L.; Nouguier, R.; Stella, L. Synlett 1998, 780; Miyabe, H.; Yoshioka, N.; Ueda, M.; Naito, T. J. Chem. Soc. Perkin Trans. 1 1998, 3659. O-centered radicals: Brown, H. C.; Midland, M. M. Angew. Chem. Int. Ed. Engl. 1972, 11, 692; Nozaki, K.; Oshima, K. Chem. Commun. 1998, 3659; Utimoto, K. Bull. Chem. Soc. Jpn. 1991, 64, 403; Clive, D. L. J.; Postema, M. H. D. J. Chem. Soc., Chem. Commun. 1993, 429; Devin, P.; Fensterbank, L.; Malacria, M. Tetrahedron Lett. 1998, 39, 833.
18. Recently, radical chain reactions involving alkylboranes and heteroatom centered radicals have been reported: N-centered radicals: Miyabe, H.; Ushiro, C.; Naito, T. Chem. Commun. 1997, 1789; Miyabe, H.; Shibata, R.; Ushiro, C.; Naito, T. Tetrahedron Lett. 1998, 39, 631; Bertrand, M. P.; Feray, L.; Nouguier, R.; Stella, L. Synlett 1998, 780; Miyabe, H.; Yoshioka, N.; Ueda, M.; Naito, T. J. Chem. Soc. Perkin Trans. 1 1998, 3659. O-centered radicals: Brown, H. C.; Midland, M. M. Angew. Chem. Int. Ed. Engl. 1972, 11, 692; Nozaki, K.; Oshima, K. Chem. Commun. 1998, 3659; Utimoto, K. Bull. Chem. Soc. Jpn. 1991, 64, 403; Clive, D. L. J.; Postema, M. H. D. J. Chem. Soc., Chem. Commun. 1993, 429; Devin, P.; Fensterbank, L.; Malacria, M. Tetrahedron Lett. 1998, 39, 833.
19. Recently, radical chain reactions involving alkylboranes and heteroatom centered radicals have been reported: N-centered radicals: Miyabe, H.; Ushiro, C.; Naito, T. Chem. Commun. 1997, 1789; Miyabe, H.; Shibata, R.; Ushiro, C.; Naito, T. Tetrahedron Lett. 1998, 39, 631; Bertrand, M. P.; Feray, L.; Nouguier, R.; Stella, L. Synlett 1998, 780; Miyabe, H.; Yoshioka, N.; Ueda, M.; Naito, T. J. Chem. Soc. Perkin Trans. 1 1998, 3659. O-centered radicals: Brown, H. C.; Midland, M. M. Angew. Chem. Int. Ed. Engl. 1972, 11, 692; Nozaki, K.; Oshima, K. Chem. Commun. 1998, 3659; Utimoto, K. Bull. Chem. Soc. Jpn. 1991, 64, 403; Clive, D. L. J.; Postema, M. H. D. J. Chem. Soc., Chem. Commun. 1993, 429; Devin, P.; Fensterbank, L.; Malacria, M. Tetrahedron Lett. 1998, 39, 833.
20. Recently, radical chain reactions involving alkylboranes and heteroatom centered radicals have been reported: N-centered radicals: Miyabe, H.; Ushiro, C.; Naito, T. Chem. Commun. 1997, 1789; Miyabe, H.; Shibata, R.; Ushiro, C.; Naito, T. Tetrahedron Lett. 1998, 39, 631; Bertrand, M. P.; Feray, L.; Nouguier, R.; Stella, L. Synlett 1998, 780; Miyabe, H.; Yoshioka, N.; Ueda, M.; Naito, T. J. Chem. Soc. Perkin Trans. 1 1998, 3659. O-centered radicals: Brown, H. C.; Midland, M. M. Angew. Chem. Int. Ed. Engl. 1972, 11, 692; Nozaki, K.; Oshima, K. Chem. Commun. 1998, 3659; Utimoto, K. Bull. Chem. Soc. Jpn. 1991, 64, 403; Clive, D. L. J.; Postema, M. H. D. J. Chem. Soc., Chem. Commun. 1993, 429; Devin, P.; Fensterbank, L.; Malacria, M. Tetrahedron Lett. 1998, 39, 833.
21. Recently, radical chain reactions involving alkylboranes and heteroatom centered radicals have been reported: N-centered radicals: Miyabe, H.; Ushiro, C.; Naito, T. Chem. Commun. 1997, 1789; Miyabe, H.; Shibata, R.; Ushiro, C.; Naito, T. Tetrahedron Lett. 1998, 39, 631; Bertrand, M. P.; Feray, L.; Nouguier, R.; Stella, L. Synlett 1998, 780; Miyabe, H.; Yoshioka, N.; Ueda, M.; Naito, T. J. Chem. Soc. Perkin Trans. 1 1998, 3659. O-centered radicals: Brown, H. C.; Midland, M. M. Angew. Chem. Int. Ed. Engl. 1972, 11, 692; Nozaki, K.; Oshima, K. Chem. Commun. 1998, 3659; Utimoto, K. Bull. Chem. Soc. Jpn. 1991, 64, 403; Clive, D. L. J.; Postema, M. H. D. J. Chem. Soc., Chem. Commun. 1993, 429; Devin, P.; Fensterbank, L.; Malacria, M. Tetrahedron Lett. 1998, 39, 833.
22. Recently, radical chain reactions involving alkylboranes and heteroatom centered radicals have been reported: N-centered radicals: Miyabe, H.; Ushiro, C.; Naito, T. Chem. Commun. 1997, 1789; Miyabe, H.; Shibata, R.; Ushiro, C.; Naito, T. Tetrahedron Lett. 1998, 39, 631; Bertrand, M. P.; Feray, L.; Nouguier, R.; Stella, L. Synlett 1998, 780; Miyabe, H.; Yoshioka, N.; Ueda, M.; Naito, T. J. Chem. Soc. Perkin Trans. 1 1998, 3659. O-centered radicals: Brown, H. C.; Midland, M. M. Angew. Chem. Int. Ed. Engl. 1972, 11, 692; Nozaki, K.; Oshima, K. Chem. Commun. 1998, 3659; Utimoto, K. Bull. Chem. Soc. Jpn. 1991, 64, 403; Clive, D. L. J.; Postema, M. H. D. J. Chem. Soc., Chem. Commun. 1993, 429; Devin, P.; Fensterbank, L.; Malacria, M. Tetrahedron Lett. 1998, 39, 833.
23. Recently, radical chain reactions involving alkylboranes and heteroatom centered radicals have been reported: N-centered radicals: Miyabe, H.; Ushiro, C.; Naito, T. Chem. Commun. 1997, 1789; Miyabe, H.; Shibata, R.; Ushiro, C.; Naito, T. Tetrahedron Lett. 1998, 39, 631; Bertrand, M. P.; Feray, L.; Nouguier, R.; Stella, L. Synlett 1998, 780; Miyabe, H.; Yoshioka, N.; Ueda, M.; Naito, T. J. Chem. Soc. Perkin Trans. 1 1998, 3659. O-centered radicals: Brown, H. C.; Midland, M. M. Angew. Chem. Int. Ed. Engl. 1972, 11, 692; Nozaki, K.; Oshima, K. Chem. Commun. 1998, 3659; Utimoto, K. Bull. Chem. Soc. Jpn. 1991, 64, 403; Clive, D. L. J.; Postema, M. H. D. J. Chem. Soc., Chem. Commun. 1993, 429; Devin, P.; Fensterbank, L.; Malacria, M. Tetrahedron Lett. 1998, 39, 833.
24. Recently, radical chain reactions involving alkylboranes and heteroatom centered radicals have been reported: N-centered radicals: Miyabe, H.; Ushiro, C.; Naito, T. Chem. Commun. 1997, 1789; Miyabe, H.; Shibata, R.; Ushiro, C.; Naito, T. Tetrahedron Lett. 1998, 39, 631; Bertrand, M. P.; Feray, L.; Nouguier, R.; Stella, L. Synlett 1998, 780; Miyabe, H.; Yoshioka, N.; Ueda, M.; Naito, T. J. Chem. Soc. Perkin Trans. 1 1998, 3659. O-centered radicals: Brown, H. C.; Midland, M. M. Angew. Chem. Int. Ed. Engl. 1972, 11, 692; Nozaki, K.; Oshima, K. Chem. Commun. 1998, 3659; Utimoto, K. Bull. Chem. Soc. Jpn. 1991, 64, 403; Clive, D. L. J.; Postema, M. H. D. J. Chem. Soc., Chem. Commun. 1993, 429; Devin, P.; Fensterbank, L.; Malacria, M. Tetrahedron Lett. 1998, 39, 833.
25. For the coupling reaction of alkyl radicals with aminoxyl radicals, see: Kinney, R. J.; Jones, W. D. J.; Bergman, R. G. J. Am. Chem. Soc. 1978, 100, 7902. Pattenden, G. Chem. Soc. Rev. 1988, 17, 361. Howel, A. R.; Pattenden, G. J. Chem. Soc., Chem. Commun. 1990, 103. Patel, V. F.; Pattenden, G.; Thompson, D. M. J. Chem. Soc. Perkin Trans. 1 1990, 2729. Ali, A.; Harrowven, D. C.; Pattenden, G. Tetrahedron Lett. 1992, 33, 2851. Barrett, A. G. M.; Bezuidenhoudt, B. C. B.; Melcher, L. M. J. Org. Chem. 1990, 55, 5196. Barrett, A. G. M.; Rys, D. J. J. Chem. Soc., Chem. Commun. 1994, 837. Hartung, J.; Giese, B. Chem. Ber. 1991, 124, 387. Boger, D. L.; McKie, J. A. J. Org. Chem. 1995, 60, 1271. Nagashima, T.; Curran, D. P. Synlett 1996, 330. Braslau, R.; Burrill, L. C.; Mahal, L. K.; Wedeking, T. Angew. Chem. Int. Ed. 1997, 36, 237. Braslau, R.; Burrill, L. C.; Chaplinski, V.; Howden, R.; Papa, P. W. Tetrahedron Asymmetry 1997, 8, 3209. Braslau, R.; Chaplinski, V.; Goodson, P. J. Org. Chem. 1998, 63, 9857. Jahn, U. J. Org. Chem. 1998, 63, 7130.
26. For the coupling reaction of alkyl radicals with aminoxyl radicals, see: Kinney, R. J.; Jones, W. D. J.; Bergman, R. G. J. Am. Chem. Soc. 1978, 100, 7902. Pattenden, G. Chem. Soc. Rev. 1988, 17, 361. Howel, A. R.; Pattenden, G. J. Chem. Soc., Chem. Commun. 1990, 103. Patel, V. F.; Pattenden, G.; Thompson, D. M. J. Chem. Soc. Perkin Trans. 1 1990, 2729. Ali, A.; Harrowven, D. C.; Pattenden, G. Tetrahedron Lett. 1992, 33, 2851. Barrett, A. G. M.; Bezuidenhoudt, B. C. B.; Melcher, L. M. J. Org. Chem. 1990, 55, 5196. Barrett, A. G. M.; Rys, D. J. J. Chem. Soc., Chem. Commun. 1994, 837. Hartung, J.; Giese, B. Chem. Ber. 1991, 124, 387. Boger, D. L.; McKie, J. A. J. Org. Chem. 1995, 60, 1271. Nagashima, T.; Curran, D. P. Synlett 1996, 330. Braslau, R.; Burrill, L. C.; Mahal, L. K.; Wedeking, T. Angew. Chem. Int. Ed. 1997, 36, 237. Braslau, R.; Burrill, L. C.; Chaplinski, V.; Howden, R.; Papa, P. W. Tetrahedron Asymmetry 1997, 8, 3209. Braslau, R.; Chaplinski, V.; Goodson, P. J. Org. Chem. 1998, 63, 9857. Jahn, U. J. Org. Chem. 1998, 63, 7130.
27. For the coupling reaction of alkyl radicals with aminoxyl radicals, see: Kinney, R. J.; Jones, W. D. J.; Bergman, R. G. J. Am. Chem. Soc. 1978, 100, 7902. Pattenden, G. Chem. Soc. Rev. 1988, 17, 361. Howel, A. R.; Pattenden, G. J. Chem. Soc., Chem. Commun. 1990, 103. Patel, V. F.; Pattenden, G.; Thompson, D. M. J. Chem. Soc. Perkin Trans. 1 1990, 2729. Ali, A.; Harrowven, D. C.; Pattenden, G. Tetrahedron Lett. 1992, 33, 2851. Barrett, A. G. M.; Bezuidenhoudt, B. C. B.; Melcher, L. M. J. Org. Chem. 1990, 55, 5196. Barrett, A. G. M.; Rys, D. J. J. Chem. Soc., Chem. Commun. 1994, 837. Hartung, J.; Giese, B. Chem. Ber. 1991, 124, 387. Boger, D. L.; McKie, J. A. J. Org. Chem. 1995, 60, 1271. Nagashima, T.; Curran, D. P. Synlett 1996, 330. Braslau, R.; Burrill, L. C.; Mahal, L. K.; Wedeking, T. Angew. Chem. Int. Ed. 1997, 36, 237. Braslau, R.; Burrill, L. C.; Chaplinski, V.; Howden, R.; Papa, P. W. Tetrahedron Asymmetry 1997, 8, 3209. Braslau, R.; Chaplinski, V.; Goodson, P. J. Org. Chem. 1998, 63, 9857. Jahn, U. J. Org. Chem. 1998, 63, 7130.
28. For the coupling reaction of alkyl radicals with aminoxyl radicals, see: Kinney, R. J.; Jones, W. D. J.; Bergman, R. G. J. Am. Chem. Soc. 1978, 100, 7902. Pattenden, G. Chem. Soc. Rev. 1988, 17, 361. Howel, A. R.; Pattenden, G. J. Chem. Soc., Chem. Commun. 1990, 103. Patel, V. F.; Pattenden, G.; Thompson, D. M. J. Chem. Soc. Perkin Trans. 1 1990, 2729. Ali, A.; Harrowven, D. C.; Pattenden, G. Tetrahedron Lett. 1992, 33, 2851. Barrett, A. G. M.; Bezuidenhoudt, B. C. B.; Melcher, L. M. J. Org. Chem. 1990, 55, 5196. Barrett, A. G. M.; Rys, D. J. J. Chem. Soc., Chem. Commun. 1994, 837. Hartung, J.; Giese, B. Chem. Ber. 1991, 124, 387. Boger, D. L.; McKie, J. A. J. Org. Chem. 1995, 60, 1271. Nagashima, T.; Curran, D. P. Synlett 1996, 330. Braslau, R.; Burrill, L. C.; Mahal, L. K.; Wedeking, T. Angew. Chem. Int. Ed. 1997, 36, 237. Braslau, R.; Burrill, L. C.; Chaplinski, V.; Howden, R.; Papa, P. W. Tetrahedron Asymmetry 1997, 8, 3209. Braslau, R.; Chaplinski, V.; Goodson, P. J. Org. Chem. 1998, 63, 9857. Jahn, U. J. Org. Chem. 1998, 63, 7130.
29. For the coupling reaction of alkyl radicals with aminoxyl radicals, see: Kinney, R. J.; Jones, W. D. J.; Bergman, R. G. J. Am. Chem. Soc. 1978, 100, 7902. Pattenden, G. Chem. Soc. Rev. 1988, 17, 361. Howel, A. R.; Pattenden, G. J. Chem. Soc., Chem. Commun. 1990, 103. Patel, V. F.; Pattenden, G.; Thompson, D. M. J. Chem. Soc. Perkin Trans. 1 1990, 2729. Ali, A.; Harrowven, D. C.; Pattenden, G. Tetrahedron Lett. 1992, 33, 2851. Barrett, A. G. M.; Bezuidenhoudt, B. C. B.; Melcher, L. M. J. Org. Chem. 1990, 55, 5196. Barrett, A. G. M.; Rys, D. J. J. Chem. Soc., Chem. Commun. 1994, 837. Hartung, J.; Giese, B. Chem. Ber. 1991, 124, 387. Boger, D. L.; McKie, J. A. J. Org. Chem. 1995, 60, 1271. Nagashima, T.; Curran, D. P. Synlett 1996, 330. Braslau, R.; Burrill, L. C.; Mahal, L. K.; Wedeking, T. Angew. Chem. Int. Ed. 1997, 36, 237. Braslau, R.; Burrill, L. C.; Chaplinski, V.; Howden, R.; Papa, P. W. Tetrahedron Asymmetry 1997, 8, 3209. Braslau, R.; Chaplinski, V.; Goodson, P. J. Org. Chem. 1998, 63, 9857. Jahn, U. J. Org. Chem. 1998, 63, 7130.
30. For the coupling reaction of alkyl radicals with aminoxyl radicals, see: Kinney, R. J.; Jones, W. D. J.; Bergman, R. G. J. Am. Chem. Soc. 1978, 100, 7902. Pattenden, G. Chem. Soc. Rev. 1988, 17, 361. Howel, A. R.; Pattenden, G. J. Chem. Soc., Chem. Commun. 1990, 103. Patel, V. F.; Pattenden, G.; Thompson, D. M. J. Chem. Soc. Perkin Trans. 1 1990, 2729. Ali, A.; Harrowven, D. C.; Pattenden, G. Tetrahedron Lett. 1992, 33, 2851. Barrett, A. G. M.; Bezuidenhoudt, B. C. B.; Melcher, L. M. J. Org. Chem. 1990, 55, 5196. Barrett, A. G. M.; Rys, D. J. J. Chem. Soc., Chem. Commun. 1994, 837. Hartung, J.; Giese, B. Chem. Ber. 1991, 124, 387. Boger, D. L.; McKie, J. A. J. Org. Chem. 1995, 60, 1271. Nagashima, T.; Curran, D. P. Synlett 1996, 330. Braslau, R.; Burrill, L. C.; Mahal, L. K.; Wedeking, T. Angew. Chem. Int. Ed. 1997, 36, 237. Braslau, R.; Burrill, L. C.; Chaplinski, V.; Howden, R.; Papa, P. W. Tetrahedron Asymmetry 1997, 8, 3209. Braslau, R.; Chaplinski, V.; Goodson, P. J. Org. Chem. 1998, 63, 9857. Jahn, U. J. Org. Chem. 1998, 63, 7130.
31. For the coupling reaction of alkyl radicals with aminoxyl radicals, see: Kinney, R. J.; Jones, W. D. J.; Bergman, R. G. J. Am. Chem. Soc. 1978, 100, 7902. Pattenden, G. Chem. Soc. Rev. 1988, 17, 361. Howel, A. R.; Pattenden, G. J. Chem. Soc., Chem. Commun. 1990, 103. Patel, V. F.; Pattenden, G.; Thompson, D. M. J. Chem. Soc. Perkin Trans. 1 1990, 2729. Ali, A.; Harrowven, D. C.; Pattenden, G. Tetrahedron Lett. 1992, 33, 2851. Barrett, A. G. M.; Bezuidenhoudt, B. C. B.; Melcher, L. M. J. Org. Chem. 1990, 55, 5196. Barrett, A. G. M.; Rys, D. J. J. Chem. Soc., Chem. Commun. 1994, 837. Hartung, J.; Giese, B. Chem. Ber. 1991, 124, 387. Boger, D. L.; McKie, J. A. J. Org. Chem. 1995, 60, 1271. Nagashima, T.; Curran, D. P. Synlett 1996, 330. Braslau, R.; Burrill, L. C.; Mahal, L. K.; Wedeking, T. Angew. Chem. Int. Ed. 1997, 36, 237. Braslau, R.; Burrill, L. C.; Chaplinski, V.; Howden, R.; Papa, P. W. Tetrahedron Asymmetry 1997, 8, 3209. Braslau, R.; Chaplinski, V.; Goodson, P. J. Org. Chem. 1998, 63, 9857. Jahn, U. J. Org. Chem. 1998, 63, 7130.
32. For the coupling reaction of alkyl radicals with aminoxyl radicals, see: Kinney, R. J.; Jones, W. D. J.; Bergman, R. G. J. Am. Chem. Soc. 1978, 100, 7902. Pattenden, G. Chem. Soc. Rev. 1988, 17, 361. Howel, A. R.; Pattenden, G. J. Chem. Soc., Chem. Commun. 1990, 103. Patel, V. F.; Pattenden, G.; Thompson, D. M. J. Chem. Soc. Perkin Trans. 1 1990, 2729. Ali, A.; Harrowven, D. C.; Pattenden, G. Tetrahedron Lett. 1992, 33, 2851. Barrett, A. G. M.; Bezuidenhoudt, B. C. B.; Melcher, L. M. J. Org. Chem. 1990, 55, 5196. Barrett, A. G. M.; Rys, D. J. J. Chem. Soc., Chem. Commun. 1994, 837. Hartung, J.; Giese, B. Chem. Ber. 1991, 124, 387. Boger, D. L.; McKie, J. A. J. Org. Chem. 1995, 60, 1271. Nagashima, T.; Curran, D. P. Synlett 1996, 330. Braslau, R.; Burrill, L. C.; Mahal, L. K.; Wedeking, T. Angew. Chem. Int. Ed. 1997, 36, 237. Braslau, R.; Burrill, L. C.; Chaplinski, V.; Howden, R.; Papa, P. W. Tetrahedron Asymmetry 1997, 8, 3209. Braslau, R.; Chaplinski, V.; Goodson, P. J. Org. Chem. 1998, 63, 9857. Jahn, U. J. Org. Chem. 1998, 63, 7130.
33. For the coupling reaction of alkyl radicals with aminoxyl radicals, see: Kinney, R. J.; Jones, W. D. J.; Bergman, R. G. J. Am. Chem. Soc. 1978, 100, 7902. Pattenden, G. Chem. Soc. Rev. 1988, 17, 361. Howel, A. R.; Pattenden, G. J. Chem. Soc., Chem. Commun. 1990, 103. Patel, V. F.; Pattenden, G.; Thompson, D. M. J. Chem. Soc. Perkin Trans. 1 1990, 2729. Ali, A.; Harrowven, D. C.; Pattenden, G. Tetrahedron Lett. 1992, 33, 2851. Barrett, A. G. M.; Bezuidenhoudt, B. C. B.; Melcher, L. M. J. Org. Chem. 1990, 55, 5196. Barrett, A. G. M.; Rys, D. J. J. Chem. Soc., Chem. Commun. 1994, 837. Hartung, J.; Giese, B. Chem. Ber. 1991, 124, 387. Boger, D. L.; McKie, J. A. J. Org. Chem. 1995, 60, 1271. Nagashima, T.; Curran, D. P. Synlett 1996, 330. Braslau, R.; Burrill, L. C.; Mahal, L. K.; Wedeking, T. Angew. Chem. Int. Ed. 1997, 36, 237. Braslau, R.; Burrill, L. C.; Chaplinski, V.; Howden, R.; Papa, P. W. Tetrahedron Asymmetry 1997, 8, 3209. Braslau, R.; Chaplinski, V.; Goodson, P. J. Org. Chem. 1998, 63, 9857. Jahn, U. J. Org. Chem. 1998, 63, 7130.
34. For the coupling reaction of alkyl radicals with aminoxyl radicals, see: Kinney, R. J.; Jones, W. D. J.; Bergman, R. G. J. Am. Chem. Soc. 1978, 100, 7902. Pattenden, G. Chem. Soc. Rev. 1988, 17, 361. Howel, A. R.; Pattenden, G. J. Chem. Soc., Chem. Commun. 1990, 103. Patel, V. F.; Pattenden, G.; Thompson, D. M. J. Chem. Soc. Perkin Trans. 1 1990, 2729. Ali, A.; Harrowven, D. C.; Pattenden, G. Tetrahedron Lett. 1992, 33, 2851. Barrett, A. G. M.; Bezuidenhoudt, B. C. B.; Melcher, L. M. J. Org. Chem. 1990, 55, 5196. Barrett, A. G. M.; Rys, D. J. J. Chem. Soc., Chem. Commun. 1994, 837. Hartung, J.; Giese, B. Chem. Ber. 1991, 124, 387. Boger, D. L.; McKie, J. A. J. Org. Chem. 1995, 60, 1271. Nagashima, T.; Curran, D. P. Synlett 1996, 330. Braslau, R.; Burrill, L. C.; Mahal, L. K.; Wedeking, T. Angew. Chem. Int. Ed. 1997, 36, 237. Braslau, R.; Burrill, L. C.; Chaplinski, V.; Howden, R.; Papa, P. W. Tetrahedron Asymmetry 1997, 8, 3209. Braslau, R.; Chaplinski, V.; Goodson, P. J. Org. Chem. 1998, 63, 9857. Jahn, U. J. Org. Chem. 1998, 63, 7130.
35. For the coupling reaction of alkyl radicals with aminoxyl radicals, see: Kinney, R. J.; Jones, W. D. J.; Bergman, R. G. J. Am. Chem. Soc. 1978, 100, 7902. Pattenden, G. Chem. Soc. Rev. 1988, 17, 361. Howel, A. R.; Pattenden, G. J. Chem. Soc., Chem. Commun. 1990, 103. Patel, V. F.; Pattenden, G.; Thompson, D. M. J. Chem. Soc. Perkin Trans. 1 1990, 2729. Ali, A.; Harrowven, D. C.; Pattenden, G. Tetrahedron Lett. 1992, 33, 2851. Barrett, A. G. M.; Bezuidenhoudt, B. C. B.; Melcher, L. M. J. Org. Chem. 1990, 55, 5196. Barrett, A. G. M.; Rys, D. J. J. Chem. Soc., Chem. Commun. 1994, 837. Hartung, J.; Giese, B. Chem. Ber. 1991, 124, 387. Boger, D. L.; McKie, J. A. J. Org. Chem. 1995, 60, 1271. Nagashima, T.; Curran, D. P. Synlett 1996, 330. Braslau, R.; Burrill, L. C.; Mahal, L. K.; Wedeking, T. Angew. Chem. Int. Ed. 1997, 36, 237. Braslau, R.; Burrill, L. C.; Chaplinski, V.; Howden, R.; Papa, P. W. Tetrahedron Asymmetry 1997, 8, 3209. Braslau, R.; Chaplinski, V.; Goodson, P. J. Org. Chem. 1998, 63, 9857. Jahn, U. J. Org. Chem. 1998, 63, 7130.
36. For the coupling reaction of alkyl radicals with aminoxyl radicals, see: Kinney, R. J.; Jones, W. D. J.; Bergman, R. G. J. Am. Chem. Soc. 1978, 100, 7902. Pattenden, G. Chem. Soc. Rev. 1988, 17, 361. Howel, A. R.; Pattenden, G. J. Chem. Soc., Chem. Commun. 1990, 103. Patel, V. F.; Pattenden, G.; Thompson, D. M. J. Chem. Soc. Perkin Trans. 1 1990, 2729. Ali, A.; Harrowven, D. C.; Pattenden, G. Tetrahedron Lett. 1992, 33, 2851. Barrett, A. G. M.; Bezuidenhoudt, B. C. B.; Melcher, L. M. J. Org. Chem. 1990, 55, 5196. Barrett, A. G. M.; Rys, D. J. J. Chem. Soc., Chem. Commun. 1994, 837. Hartung, J.; Giese, B. Chem. Ber. 1991, 124, 387. Boger, D. L.; McKie, J. A. J. Org. Chem. 1995, 60, 1271. Nagashima, T.; Curran, D. P. Synlett 1996, 330. Braslau, R.; Burrill, L. C.; Mahal, L. K.; Wedeking, T. Angew. Chem. Int. Ed. 1997, 36, 237. Braslau, R.; Burrill, L. C.; Chaplinski, V.; Howden, R.; Papa, P. W. Tetrahedron Asymmetry 1997, 8, 3209. Braslau, R.; Chaplinski, V.; Goodson, P. J. Org. Chem. 1998, 63, 9857. Jahn, U. J. Org. Chem. 1998, 63, 7130.
37. For the coupling reaction of alkyl radicals with aminoxyl radicals, see: Kinney, R. J.; Jones, W. D. J.; Bergman, R. G. J. Am. Chem. Soc. 1978, 100, 7902. Pattenden, G. Chem. Soc. Rev. 1988, 17, 361. Howel, A. R.; Pattenden, G. J. Chem. Soc., Chem. Commun. 1990, 103. Patel, V. F.; Pattenden, G.; Thompson, D. M. J. Chem. Soc. Perkin Trans. 1 1990, 2729. Ali, A.; Harrowven, D. C.; Pattenden, G. Tetrahedron Lett. 1992, 33, 2851. Barrett, A. G. M.; Bezuidenhoudt, B. C. B.; Melcher, L. M. J. Org. Chem. 1990, 55, 5196. Barrett, A. G. M.; Rys, D. J. J. Chem. Soc., Chem. Commun. 1994, 837. Hartung, J.; Giese, B. Chem. Ber. 1991, 124, 387. Boger, D. L.; McKie, J. A. J. Org. Chem. 1995, 60, 1271. Nagashima, T.; Curran, D. P. Synlett 1996, 330. Braslau, R.; Burrill, L. C.; Mahal, L. K.; Wedeking, T. Angew. Chem. Int. Ed. 1997, 36, 237. Braslau, R.; Burrill, L. C.; Chaplinski, V.; Howden, R.; Papa, P. W. Tetrahedron Asymmetry 1997, 8, 3209. Braslau, R.; Chaplinski, V.; Goodson, P. J. Org. Chem. 1998, 63, 9857. Jahn, U. J. Org. Chem. 1998, 63, 7130.
38. For the coupling reaction of alkyl radicals with aminoxyl radicals, see: Kinney, R. J.; Jones, W. D. J.; Bergman, R. G. J. Am. Chem. Soc. 1978, 100, 7902. Pattenden, G. Chem. Soc. Rev. 1988, 17, 361. Howel, A. R.; Pattenden, G. J. Chem. Soc., Chem. Commun. 1990, 103. Patel, V. F.; Pattenden, G.; Thompson, D. M. J. Chem. Soc. Perkin Trans. 1 1990, 2729. Ali, A.; Harrowven, D. C.; Pattenden, G. Tetrahedron Lett. 1992, 33, 2851. Barrett, A. G. M.; Bezuidenhoudt, B. C. B.; Melcher, L. M. J. Org. Chem. 1990, 55, 5196. Barrett, A. G. M.; Rys, D. J. J. Chem. Soc., Chem. Commun. 1994, 837. Hartung, J.; Giese, B. Chem. Ber. 1991, 124, 387. Boger, D. L.; McKie, J. A. J. Org. Chem. 1995, 60, 1271. Nagashima, T.; Curran, D. P. Synlett 1996, 330. Braslau, R.; Burrill, L. C.; Mahal, L. K.; Wedeking, T. Angew. Chem. Int. Ed. 1997, 36, 237. Braslau, R.; Burrill, L. C.; Chaplinski, V.; Howden, R.; Papa, P. W. Tetrahedron Asymmetry 1997, 8, 3209. Braslau, R.; Chaplinski, V.; Goodson, P. J. Org. Chem. 1998, 63, 9857. Jahn, U. J. Org. Chem. 1998, 63, 7130.
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42. 18O (154.25): calcd: C 77.87, H 11.76; found: C 77.39, H 11.60.
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