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Volumn 30, Issue 3, 1997, Pages 131-137

Investigation of the Early Steps in Electrophilic Bromination through the Study of the Reaction with Sterically Encumbered Olefins

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EID: 0001349866     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar960088e     Document Type: Article
Times cited : (193)

References (72)
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    • For reviews of the general literature see: (a) DeLaMare, P. B. D.; Bolton, R. Electrophilic Additions to Unsaturated Systems, 2nd ed.; Elsevier: New York, 1982; pp 136-197. (b) V'yunov, K. A.; Ginak, A. I. Russ. Chem. Rev. (Engl. Transl.) 1981, 50, 151. (c) Schmid, G. H.; Garrat, D. G. In The Chemistry of Double Bonded Functional Groups; Patai, S., Ed.; Wiley: New York, 1977; Suppl. A, Part 2, p 725. (d) Schmid, G. H. In The Chemistry of Double-Bonded Functional Groups; Patai, S., Ed.; Wiley: New York, 1989; Suppl. A, Vol. 3, Part 1, p 699. (e) Ruasse, M.-F. Adv. Phys. Org. Chem. 1993, 28, 207.
    • (1981) Russ. Chem. Rev. (Engl. Transl.) , vol.50 , pp. 151
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    • Patai, S., Ed.; Wiley: New York
    • For reviews of the general literature see: (a) DeLaMare, P. B. D.; Bolton, R. Electrophilic Additions to Unsaturated Systems, 2nd ed.; Elsevier: New York, 1982; pp 136-197. (b) V'yunov, K. A.; Ginak, A. I. Russ. Chem. Rev. (Engl. Transl.) 1981, 50, 151. (c) Schmid, G. H.; Garrat, D. G. In The Chemistry of Double Bonded Functional Groups; Patai, S., Ed.; Wiley: New York, 1977; Suppl. A, Part 2, p 725. (d) Schmid, G. H. In The Chemistry of Double-Bonded Functional Groups; Patai, S., Ed.; Wiley: New York, 1989; Suppl. A, Vol. 3, Part 1, p 699. (e) Ruasse, M.-F. Adv. Phys. Org. Chem. 1993, 28, 207.
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    • For reviews of the general literature see: (a) DeLaMare, P. B. D.; Bolton, R. Electrophilic Additions to Unsaturated Systems, 2nd ed.; Elsevier: New York, 1982; pp 136-197. (b) V'yunov, K. A.; Ginak, A. I. Russ. Chem. Rev. (Engl. Transl.) 1981, 50, 151. (c) Schmid, G. H.; Garrat, D. G. In The Chemistry of Double Bonded Functional Groups; Patai, S., Ed.; Wiley: New York, 1977; Suppl. A, Part 2, p 725. (d) Schmid, G. H. In The Chemistry of Double-Bonded Functional Groups; Patai, S., Ed.; Wiley: New York, 1989; Suppl. A, Vol. 3, Part 1, p 699. (e) Ruasse, M.-F. Adv. Phys. Org. Chem. 1993, 28, 207.
    • (1989) The Chemistry of Double-Bonded Functional Groups , vol.3 , Issue.1 SUPPL. A , pp. 699
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    • For reviews of the general literature see: (a) DeLaMare, P. B. D.; Bolton, R. Electrophilic Additions to Unsaturated Systems, 2nd ed.; Elsevier: New York, 1982; pp 136-197. (b) V'yunov, K. A.; Ginak, A. I. Russ. Chem. Rev. (Engl. Transl.) 1981, 50, 151. (c) Schmid, G. H.; Garrat, D. G. In The Chemistry of Double Bonded Functional Groups; Patai, S., Ed.; Wiley: New York, 1977; Suppl. A, Part 2, p 725. (d) Schmid, G. H. In The Chemistry of Double-Bonded Functional Groups; Patai, S., Ed.; Wiley: New York, 1989; Suppl. A, Vol. 3, Part 1, p 699. (e) Ruasse, M.-F. Adv. Phys. Org. Chem. 1993, 28, 207.
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    • For reviews of specific aspects of electrophilic bromination such as nucleophilic solvent assistance and open vs closed ionic intermediates see: (a) Ruasse, M.-F.; Motallebi, S. J. Phys. Org. Chem. 1991, 4, 527. (b) Ruasse, M.-F. Acc. Chem. Res. 1990, 23, 87.
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  • 7
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    • For reviews of specific aspects of electrophilic bromination such as nucleophilic solvent assistance and open vs closed ionic intermediates see: (a) Ruasse, M.-F.; Motallebi, S. J. Phys. Org. Chem. 1991, 4, 527. (b) Ruasse, M.-F. Acc. Chem. Res. 1990, 23, 87.
    • (1990) Acc. Chem. Res. , vol.23 , pp. 87
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    • (b) Fukuzumi, S.; Kochi, J. K. J. Am. Chem. Soc. 1981, 103, 2783; 1982, 104, 7599.
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    • note
    • -1 (ref 13). It was reasonably suggested (ref 2b, footnote 17b) that since Ad=Ad cannot proceed to products, its behavior and perhaps physicochemical properties were not representative of those of more normal olefins.
  • 36
    • 0003243956 scopus 로고
    • 2. Examination of molecular models indicates that this olefin may also form a CTC which is prevented, by steric compression, from proceeding to the bromonium ion.
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    • Olefin 27 was originally reported to brominate to give 28 by Bartlett and Ho (Bartlett, P. D.; Ho, M. S. J. Am. Chem. Soc. 1974, 96, 627).
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    • note
    • 33


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