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Volumn 125, Issue 11, 2003, Pages 3248-3259

Trimethyl phosphite as a trap for alkoxy radicals formed from the ring opening of oxiranylcarbinyl radicals. Conversion to alkenes. Mechanistic applications to the study of C-C versus C-O ring cleavage

Author keywords

[No Author keywords available]

Indexed keywords

RADICAL SYSTEMS;

EID: 0037454304     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja020761x     Document Type: Article
Times cited : (24)

References (44)
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    • note
    • 3SnH ratios of 500 and 400, respectively.
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    • Without resonance stabilization of 4, alcohol from allyloxy radicals (3) is formed exclusively. See. for example: Edwards, A. J.; Hird, N. W.; Marples, B. A.; Rudderman, J. A.; Slawin, A. M. Z. Tetrahedron Lett. 1997, 38, 3599. Rawal, W. H.; Zhong, H. M. Tetr Tetrahedron Lett. 1993, 55, 5181. Breen, A. P.; Murphy, J. A. J. Chem. Soc., Chem. Commun. 1993, 191. Barton, D. H. R.; Motherwell, R. S. H.; Motherwell, W. B. J. Chem. Soc., Perkin Trans. 1 1981, 2363. Johns, A.; Murphy, J. Tetrahedron Lett. 1988, 837. Davies, A. G.; Muggleton, B. J. J. Am. Chem. Soc. 1979, 101, Johns, A.; Murphy, J. Tetrahedron Lett. 1988, 837. Davies, A. G.; Tse, M. W. J. Organomet. Chem. 1978, 155, 25. Dobbs, A. J.; Gilbert, B. C.; Laue, H. A.; Norman, R. O. C. J. Chem. Soc., Perkin Trans. 2 1976, 1044.
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    • Without resonance stabilization of 4, alcohol from allyloxy radicals (3) is formed exclusively. See. for example: Edwards, A. J.; Hird, N. W.; Marples, B. A.; Rudderman, J. A.; Slawin, A. M. Z. Tetrahedron Lett. 1997, 38, 3599. Rawal, W. H.; Zhong, H. M. Tetr Tetrahedron Lett. 1993, 55, 5181. Breen, A. P.; Murphy, J. A. J. Chem. Soc., Chem. Commun. 1993, 191. Barton, D. H. R.; Motherwell, R. S. H.; Motherwell, W. B. J. Chem. Soc., Perkin Trans. 1 1981, 2363. Johns, A.; Murphy, J. Tetrahedron Lett. 1988, 837. Davies, A. G.; Muggleton, B. J. J. Am. Chem. Soc. 1979, 101, Johns, A.; Murphy, J. Tetrahedron Lett. 1988, 837. Davies, A. G.; Tse, M. W. J. Organomet. Chem. 1978, 155, 25. Dobbs, A. J.; Gilbert, B. C.; Laue, H. A.; Norman, R. O. C. J. Chem. Soc., Perkin Trans. 2 1976, 1044.
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  • 19
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    • Without resonance stabilization of 4, alcohol from allyloxy radicals (3) is formed exclusively. See. for example: Edwards, A. J.; Hird, N. W.; Marples, B. A.; Rudderman, J. A.; Slawin, A. M. Z. Tetrahedron Lett. 1997, 38, 3599. Rawal, W. H.; Zhong, H. M. Tetr Tetrahedron Lett. 1993, 55, 5181. Breen, A. P.; Murphy, J. A. J. Chem. Soc., Chem. Commun. 1993, 191. Barton, D. H. R.; Motherwell, R. S. H.; Motherwell, W. B. J. Chem. Soc., Perkin Trans. 1 1981, 2363. Johns, A.; Murphy, J. Tetrahedron Lett. 1988, 837. Davies, A. G.; Muggleton, B. J. J. Am. Chem. Soc. 1979, 101, Johns, A.; Murphy, J. Tetrahedron Lett. 1988, 837. Davies, A. G.; Tse, M. W. J. Organomet. Chem. 1978, 155, 25. Dobbs, A. J.; Gilbert, B. C.; Laue, H. A.; Norman, R. O. C. J. Chem. Soc., Perkin Trans. 2 1976, 1044.
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    • Barton, D.H.R.1    Motherwell, R.S.H.2    Motherwell, W.B.3
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    • Without resonance stabilization of 4, alcohol from allyloxy radicals (3) is formed exclusively. See. for example: Edwards, A. J.; Hird, N. W.; Marples, B. A.; Rudderman, J. A.; Slawin, A. M. Z. Tetrahedron Lett. 1997, 38, 3599. Rawal, W. H.; Zhong, H. M. Tetr Tetrahedron Lett. 1993, 55, 5181. Breen, A. P.; Murphy, J. A. J. Chem. Soc., Chem. Commun. 1993, 191. Barton, D. H. R.; Motherwell, R. S. H.; Motherwell, W. B. J. Chem. Soc., Perkin Trans. 1 1981, 2363. Johns, A.; Murphy, J. Tetrahedron Lett. 1988, 837. Davies, A. G.; Muggleton, B. J. J. Am. Chem. Soc. 1979, 101, Johns, A.; Murphy, J. Tetrahedron Lett. 1988, 837. Davies, A. G.; Tse, M. W. J. Organomet. Chem. 1978, 155, 25. Dobbs, A. J.; Gilbert, B. C.; Laue, H. A.; Norman, R. O. C. J. Chem. Soc., Perkin Trans. 2 1976, 1044.
    • (1988) Tetrahedron Lett. , pp. 837
    • Johns, A.1    Murphy, J.2
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    • Without resonance stabilization of 4, alcohol from allyloxy radicals (3) is formed exclusively. See. for example: Edwards, A. J.; Hird, N. W.; Marples, B. A.; Rudderman, J. A.; Slawin, A. M. Z. Tetrahedron Lett. 1997, 38, 3599. Rawal, W. H.; Zhong, H. M. Tetr Tetrahedron Lett. 1993, 55, 5181. Breen, A. P.; Murphy, J. A. J. Chem. Soc., Chem. Commun. 1993, 191. Barton, D. H. R.; Motherwell, R. S. H.; Motherwell, W. B. J. Chem. Soc., Perkin Trans. 1 1981, 2363. Johns, A.; Murphy, J. Tetrahedron Lett. 1988, 837. Davies, A. G.; Muggleton, B. J. J. Am. Chem. Soc. 1979, 101, Johns, A.; Murphy, J. Tetrahedron Lett. 1988, 837. Davies, A. G.; Tse, M. W. J. Organomet. Chem. 1978, 155, 25. Dobbs, A. J.; Gilbert, B. C.; Laue, H. A.; Norman, R. O. C. J. Chem. Soc., Perkin Trans. 2 1976, 1044.
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    • Without resonance stabilization of 4, alcohol from allyloxy radicals (3) is formed exclusively. See. for example: Edwards, A. J.; Hird, N. W.; Marples, B. A.; Rudderman, J. A.; Slawin, A. M. Z. Tetrahedron Lett. 1997, 38, 3599. Rawal, W. H.; Zhong, H. M. Tetr Tetrahedron Lett. 1993, 55, 5181. Breen, A. P.; Murphy, J. A. J. Chem. Soc., Chem. Commun. 1993, 191. Barton, D. H. R.; Motherwell, R. S. H.; Motherwell, W. B. J. Chem. Soc., Perkin Trans. 1 1981, 2363. Johns, A.; Murphy, J. Tetrahedron Lett. 1988, 837. Davies, A. G.; Muggleton, B. J. J. Am. Chem. Soc. 1979, 101, Johns, A.; Murphy, J. Tetrahedron Lett. 1988, 837. Davies, A. G.; Tse, M. W. J. Organomet. Chem. 1978, 155, 25. Dobbs, A. J.; Gilbert, B. C.; Laue, H. A.; Norman, R. O. C. J. Chem. Soc., Perkin Trans. 2 1976, 1044.
    • (1978) J. Organomet. Chem. , vol.155 , pp. 25
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    • Without resonance stabilization of 4, alcohol from allyloxy radicals (3) is formed exclusively. See. for example: Edwards, A. J.; Hird, N. W.; Marples, B. A.; Rudderman, J. A.; Slawin, A. M. Z. Tetrahedron Lett. 1997, 38, 3599. Rawal, W. H.; Zhong, H. M. Tetr Tetrahedron Lett. 1993, 55, 5181. Breen, A. P.; Murphy, J. A. J. Chem. Soc., Chem. Commun. 1993, 191. Barton, D. H. R.; Motherwell, R. S. H.; Motherwell, W. B. J. Chem. Soc., Perkin Trans. 1 1981, 2363. Johns, A.; Murphy, J. Tetrahedron Lett. 1988, 837. Davies, A. G.; Muggleton, B. J. J. Am. Chem. Soc. 1979, 101, Johns, A.; Murphy, J. Tetrahedron Lett. 1988, 837. Davies, A. G.; Tse, M. W. J. Organomet. Chem. 1978, 155, 25. Dobbs, A. J.; Gilbert, B. C.; Laue, H. A.; Norman, R. O. C. J. Chem. Soc., Perkin Trans. 2 1976, 1044.
    • (1976) J. Chem. Soc., Perkin Trans. 2 , pp. 1044
    • Dobbs, A.J.1    Gilbert, B.C.2    Laue, H.A.3    Norman, R.O.C.4
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    • 1 = Ph), as it does in the radical system from 12.
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