Inverse phase transfer catalysis: kinetics of the pyridine 1-oxide-catalyzed two-phase reactions of fluoro- and butyl-benzoyl chlorides and benzoate ions

Add time:09/30/2019    Source:infona.pl

The substitution reactions of XC 6 H 4 COCl (X=2-F, 3-F, 4-F, or 4-(CH 3 ) 3 C) and YC 6 H 4 COONa (Y=2-F, 3-F, 4-F, or H) in a two-phase H 2 O/CH 2 Cl 2 medium using pyridine 1-oxide (PNO) as an inverse phase transfer catalyst were investigated. Under suitable reaction conditions, the kinetics of the reaction follows a pseudo-first-order rate law, with a constant observed rate being a linear function of the concentration of PNO in the water phase. The order of reactivities of XC 6 H 4 COCl toward reaction with PNO is 2-FC 6 H 4 COCl>3-FC 6 H 4 COCl>4-FC 6 H 4 COCl>C 6 H 5 COCl>4-(CH 3 ) 3 CC 6 H 4 COCl. The order of reactivities of YC 6 H 4 COO - ions toward reaction with 1-(benzoyloxy)pyridinium (C 6 H 5 COONP + ) ion is C 6 H 5 COO - >3-FC 6 H 4 COO - >4-FC 6 H 4 COO - >2-FC 6 H 4 COO - . For the water phase with pH>12, the reaction is complicated by the competitive reaction of XC 6 H 4 COCl and OH - ion in the organic phase.

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