Substituent effect of the pentafluorophenyl group. Is there a correlation between x-ray crystal structures and reactivity in carbocation formation?

…, JM Kwong-Chip, J Mistry, JF Sawyer…

文献索引：Allen, Annette D.; Kwong-Chip, Jean Marc; Mistry, Jayant; Sawyer, Jeffery F.; Tidwell, Thomas T. Journal of Organic Chemistry, 1987 , vol. 52, # 19 p. 4164 - 4171

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被引用次数: 8

摘要

The reactivity of C6F5CH (OTs) CH3 (7) in various solvents is found to be less than that of PhCH (OTs) CH, by factors of 6 X lo3 to 5 X lo5, but the CsF5 substituent is still much more activating than hydrogen. The reactivity of 7 gives a poor correlation with the YoTs measure of solvent ionizing power, with an m value of 0.44, and while the reaction in TFA or HFIP evidently involves initial formation of an ion pair, there is strong nucleophilic assistance to ...