Tetrahedron p. 2635 - 2642 (1985)
Update date:2022-08-03
Topics:
Lee, Ikchoon
Lee, Won Heuy
Sohn, Se Chul
Kim, Choong Shik
Kinetic studies on nucleophilic substitution reaction of benzyl tosylates with anilines are reported.The reaction was found to proceed via a dissociative SN2 mechanism with less than 50 percent bond formation and extensive bond breaking at the transition state.It was found that positive charge development at the benzylic carbon is substantial and para-substituent effect on the substrate is predominantly of resonance type.Bond formation is shown to be favored by a better nucleophile, by an electron withdrawing group on the substrate and by the more polar(higher MeCN content) solvent.The substrate, nucleophile and solvent were found to follow the RSP.
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