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Volumn 48, Issue 46, 2007, Pages 8097-8100

Thermally generated phenylcarbenium ions: acid-free and self-quenching Friedel-Crafts reactions

Author keywords

[No Author keywords available]

Indexed keywords

DIAZONIUM COMPOUND; PHENYLCARBENIUM ION; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PYRIDINIUM DERIVATIVE; UNCLASSIFIED DRUG;

EID: 35348912446     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.09.116     Document Type: Article
Times cited : (14)

References (50)
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    • and references cited therein
    • Vilotijevic I., and Jamison T.F. Science 317 (2007) 1189 and references cited therein
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  • 31
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    • 2-Benzyloxy-1-methylpyridinium triflate [26189-59-3] is licensed, manufactured, and distributed non-exclusively by Sigma-Aldrich Chemical Co., catalog #679674; see: Dudley, G. B. Compounds and methods of arylmethylation (benzylation) as protection for alcohol groups. U.S. Patent Appl. 11/399,300, 2006.
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    • For the synthesis of PMB ethers, see:
    • For the synthesis of PMB ethers, see:. Nwoye E.O., and Dudley G.B. Chem. Commun. (2007) 1436
    • (2007) Chem. Commun. , pp. 1436
    • Nwoye, E.O.1    Dudley, G.B.2
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    • note
    • 1H NMR spectroscopy and provided characterization data in accord with the literature reports.
  • 39
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    • Triflic acid is one of the most acidic monoprotic acids known and readily protonates sulfuric acid.
    • Triflic acid is one of the most acidic monoprotic acids known and readily protonates sulfuric acid. Howells R.D., and McCown J.D. Chem. Rev. 77 (1965) 69
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    • Howells, R.D.1    McCown, J.D.2
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    • 3) δ 149.7, 139.0, 129.1, 128.5, 126.8, 126.7, 116.5, 112.3, 56.6, 38.5. For full characterization, see:
    • 3) δ 149.7, 139.0, 129.1, 128.5, 126.8, 126.7, 116.5, 112.3, 56.6, 38.5. For full characterization, see:. Desmarets C., Schneider R., and Fort Y. J. Org. Chem. 67 (2002) 3029
    • (2002) J. Org. Chem. , vol.67 , pp. 3029
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  • 48
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    • Friedel-Crafts alkylations of electron-rich arenes are thought to have early transition states with little σ-bond character between the electrophile and arene. Therefore, the o/p selectivity is generally modest. Less activated arene substrates react through later transition states, which usually translate to higher para-selectivity (cf. entries 2 and 6). For further discussion, see:, Wiley and Sons: Hoboken, NJ pp 670-671
    • Friedel-Crafts alkylations of electron-rich arenes are thought to have early transition states with little σ-bond character between the electrophile and arene. Therefore, the o/p selectivity is generally modest. Less activated arene substrates react through later transition states, which usually translate to higher para-selectivity (cf. entries 2 and 6). For further discussion, see:. March J., and Smith M.B. Advanced Organic Chemistry: Reactions, Mechanism, and Structure. 6th ed. (2007), Wiley and Sons: Hoboken, NJ pp 670-671
    • (2007) Advanced Organic Chemistry: Reactions, Mechanism, and Structure. 6th ed.
    • March, J.1    Smith, M.B.2
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    • note
    • 23a,b note that the formation of benzyl ether takes precedence over Friedel-Crafts chemistry.{A figure is presented}


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.