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Volumn 69, Issue 11, 1996, Pages 3345-3353

Reactivities of Stable Rotamers. XXXVIII. Reaction of Chlorine with 1-(9-Fluorenyl)-2-(1-methylethenyl)naphthalene Rotamers: Outstanding Solvent Effects on Product Distribution and Ritter Type Reactions in Acetonitrile

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EID: 0013502017     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.69.3345     Document Type: Article
Times cited : (6)

References (28)
  • 6
    • 85033821249 scopus 로고    scopus 로고
    • note
    • If an open cation is produced, it is rather unstable in nonpolar solvents and deprotonation takes place very rapidly. Deprotonation from the chloronium ion can be considered rather slow because the cationic charge is not adjacent to the methyl or the chloromethyl group. Indeed, chloro-olefins are not formed in addition reactions of chlorine to normal olefins, in which the cyclic chloronium ion intermediate is proposed. When there is a rapid equilibrium between the open and the ring cations, the long lifetime in polar solvents means that the open-cation has chances to go back to the cyclic one, where the reaction takes place to produce the adduct. Solvation of the open cation in polar solvents also retards deprotonation by neutralizing the positive charge on the carbon and, when the solvent molecule leaves the cationic center, the movement being required for formation of the adduct, the rapid deprotonation takes place rather than the attack of the chloride ion on the cation.
  • 11
    • 85033817190 scopus 로고
    • S. S. Skorokhodov, S. G. Ershova, N. V. Mikhailova, and A. A. Vansheidt, Zh. Ohshch. Khim., 31, 3626 (1961); Chem. Abstr., 57, 8555f (1962).
    • (1962) Chem. Abstr. , vol.57
  • 16
    • 0242352758 scopus 로고
    • H. E. Heine, Angew. Chem., 74, 772 (1962); Angew. Chem., Int. Ed. Engl., 1, 528 (1962).
    • (1962) Angew. Chem. , vol.74 , pp. 772
    • Heine, H.E.1
  • 17
    • 84995196424 scopus 로고
    • H. E. Heine, Angew. Chem., 74, 772 (1962); Angew. Chem., Int. Ed. Engl., 1, 528 (1962).
    • (1962) Angew. Chem., Int. Ed. Engl. , vol.1 , pp. 528


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.