109568-82-3Relevant academic research and scientific papers
Kinetics and mechanism of the aminolysis of phenyl cyclopropanecarboxylates in acetonitrile
Koh, Han Joong,Shin, Chul Ho,Lee, Hai Whang,Lee, Ikchoon
, p. 1329 - 1332 (1998)
Kinetic studies of the reaction of Z-phenyl cyclopropanecarboxylates with X-benzylamines in acetonitrile at 55.0 °C have been carried out. The reaction proceeds by a stepwise mechanism in which the rate-determining step is the breakdown of the zwitterionic tetrahedral intermediate, T±, with a hydrogen-bonded four-center type transition state (TS). These mechanistic conclusions are drawn based on (i) the large magnitude of ρX and ρZ, (ii) the normal kinetic isotope effects (KH/kD > 1.0) involving deuterated benzylamine nucleophiles, (iii) the positive sign of ρXZ and the larger magnitude of ρXZ than that for normal SN2 processes, and lastly (iv) adherence to the reactivity-selectivity principle (RSP) in all cases.
