4606-98-8Relevant articles and documents
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Swain,C.G. et al.
, p. 2534 - 2536 (1968)
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NUCLEOPHILIC SUBSTITUTION REACTION OF BENZYL BENZENESULFONATES WITH ANILINES IN MeOH-MeCN MIXTURES-I. EFFECTS OF SUBSTITUENT AND SOLVENT ON THE TRANSITION-STATE STRUCTURE.
Lee, Ikchoon,Lee, Won Heuy,Sohn, Se Chul,Kim, Choong Shik
, p. 2635 - 2642 (2007/10/02)
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.