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Volumn 82, Issue 2, 2004, Pages 75-79

The β-(acyloxy)alkyl radical rearrangement revisited

Author keywords

Contact ion pair; Radical; Rearrangement

Indexed keywords

AMMONIUM COMPOUNDS; CARBOXYLATION; PROBES; SALTS; SOLUTIONS;

EID: 2342526566     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v03-148     Document Type: Article
Times cited : (9)

References (35)
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    • Pertinent earlier mechanistic studies: (a) L.R.C. Barclay, D. Griller, and K.U. Ingold. J. Am. Chem. Soc. 104, 4399 (1982); (b) A.L.J. Beckwith and C.B. Thomas. J. Chem. Soc. Perkin Trans. 2, 861 (1973); (c) L.R.C. Barclay, J. Lusztyk, and K.U. Ingold. J. Am. Chem. Soc. 106, 1793 (1984); (d) P. Kocovsky, I. Stary, and F. Turecek. Tetrahedron Lett. 27, 1513 (1986); (e) A.L.J. Beckwith and P.J. Duggan. J. Am. Chem. Soc. 118, 12 838 (1996).
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    • Pertinent earlier mechanistic studies: (a) L.R.C. Barclay, D. Griller, and K.U. Ingold. J. Am. Chem. Soc. 104, 4399 (1982); (b) A.L.J. Beckwith and C.B. Thomas. J. Chem. Soc. Perkin Trans. 2, 861 (1973); (c) L.R.C. Barclay, J. Lusztyk, and K.U. Ingold. J. Am. Chem. Soc. 106, 1793 (1984); (d) P. Kocovsky, I. Stary, and F. Turecek. Tetrahedron Lett. 27, 1513 (1986); (e) A.L.J. Beckwith and P.J. Duggan. J. Am. Chem. Soc. 118, 12 838 (1996).
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    • Pertinent earlier mechanistic studies: (a) L.R.C. Barclay, D. Griller, and K.U. Ingold. J. Am. Chem. Soc. 104, 4399 (1982); (b) A.L.J. Beckwith and C.B. Thomas. J. Chem. Soc. Perkin Trans. 2, 861 (1973); (c) L.R.C. Barclay, J. Lusztyk, and K.U. Ingold. J. Am. Chem. Soc. 106, 1793 (1984); (d) P. Kocovsky, I. Stary, and F. Turecek. Tetrahedron Lett. 27, 1513 (1986); (e) A.L.J. Beckwith and P.J. Duggan. J. Am. Chem. Soc. 118, 12 838 (1996).
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    • For radical generation by intramolecular homolytic substitution at sulfur see (a) K.U. Ingold and B.P. Roberts. Free radical substitution reactions: Bimolecular homolytic substitutions at saturated multivalent atoms. Wiley, New York. 1971; (b) J.A. Kampmeier, R.B. Jordan, M.S. Liu, H. Yamanaka, and D.J. Bishop. In Organic free radicals. ACS Symposium Series. No 69. Edited by W.A. Pryor. ACS, Washington. 1978. pp. 275; (c) C.H. Schiesser and L.M. Wild. Tetrahedron, 52, 13265 (1996); (d) T. Ooi, M. Furuya, D. Sakai, and K. Maruoka. Adv. Synth. Catal. 343, 166 (2001); (e) D. Crich and Q. Yao. J. Org. Chem. 61, 3566 (1996).
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    • Organic free radicals. Edited by W.A. Pryor. ACS, Washington
    • For radical generation by intramolecular homolytic substitution at sulfur see (a) K.U. Ingold and B.P. Roberts. Free radical substitution reactions: Bimolecular homolytic substitutions at saturated multivalent atoms. Wiley, New York. 1971; (b) J.A. Kampmeier, R.B. Jordan, M.S. Liu, H. Yamanaka, and D.J. Bishop. In Organic free radicals. ACS Symposium Series. No 69. Edited by W.A. Pryor. ACS, Washington. 1978. pp. 275; (c) C.H. Schiesser and L.M. Wild. Tetrahedron, 52, 13265 (1996); (d) T. Ooi, M. Furuya, D. Sakai, and K. Maruoka. Adv. Synth. Catal. 343, 166 (2001); (e) D. Crich and Q. Yao. J. Org. Chem. 61, 3566 (1996).
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    • 0030583482 scopus 로고    scopus 로고
    • For radical generation by intramolecular homolytic substitution at sulfur see (a) K.U. Ingold and B.P. Roberts. Free radical substitution reactions: Bimolecular homolytic substitutions at saturated multivalent atoms. Wiley, New York. 1971; (b) J.A. Kampmeier, R.B. Jordan, M.S. Liu, H. Yamanaka, and D.J. Bishop. In Organic free radicals. ACS Symposium Series. No 69. Edited by W.A. Pryor. ACS, Washington. 1978. pp. 275; (c) C.H. Schiesser and L.M. Wild. Tetrahedron, 52, 13265 (1996); (d) T. Ooi, M. Furuya, D. Sakai, and K. Maruoka. Adv. Synth. Catal. 343, 166 (2001); (e) D. Crich and Q. Yao. J. Org. Chem. 61, 3566 (1996).
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    • Schiesser, C.H.1    Wild, L.M.2
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    • 0004910274 scopus 로고    scopus 로고
    • For radical generation by intramolecular homolytic substitution at sulfur see (a) K.U. Ingold and B.P. Roberts. Free radical substitution reactions: Bimolecular homolytic substitutions at saturated multivalent atoms. Wiley, New York. 1971; (b) J.A. Kampmeier, R.B. Jordan, M.S. Liu, H. Yamanaka, and D.J. Bishop. In Organic free radicals. ACS Symposium Series. No 69. Edited by W.A. Pryor. ACS, Washington. 1978. pp. 275; (c) C.H. Schiesser and L.M. Wild. Tetrahedron, 52, 13265 (1996); (d) T. Ooi, M. Furuya, D. Sakai, and K. Maruoka. Adv. Synth. Catal. 343, 166 (2001); (e) D. Crich and Q. Yao. J. Org. Chem. 61, 3566 (1996).
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    • Ooi, T.1    Furuya, M.2    Sakai, D.3    Maruoka, K.4
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    • For radical generation by intramolecular homolytic substitution at sulfur see (a) K.U. Ingold and B.P. Roberts. Free radical substitution reactions: Bimolecular homolytic substitutions at saturated multivalent atoms. Wiley, New York. 1971; (b) J.A. Kampmeier, R.B. Jordan, M.S. Liu, H. Yamanaka, and D.J. Bishop. In Organic free radicals. ACS Symposium Series. No 69. Edited by W.A. Pryor. ACS, Washington. 1978. pp. 275; (c) C.H. Schiesser and L.M. Wild. Tetrahedron, 52, 13265 (1996); (d) T. Ooi, M. Furuya, D. Sakai, and K. Maruoka. Adv. Synth. Catal. 343, 166 (2001); (e) D. Crich and Q. Yao. J. Org. Chem. 61, 3566 (1996).
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    • Crich, D.1    Yao, Q.2


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