Journal of Organic Chemistry p. 4157 - 4160 (1984)
Update date:2022-08-16
Topics:
Chuchani, Gabriel
Rotinov, Alexandra
Dominguez, Rosa M.
Gonzalez, Neil
The gas-phase elimination kinetics of some amino esters and a keto acetate have been studied in the temperature region of 260.0-411.5 deg C and in the pressure range of 21.5-170.0 torr.These eliminations, in vessels seasoned with allyl bromide, are predominantly unimolecular and homogenous and obey a first order rate law.The rate coefficients for the reactions are expressible by the following Arrhenius equations: for 3-(dimethylamino)-1-propyl acetate (1), log k1 (s-1) = (12.97 +/- 0.20) - (202.1 +/- 2.5) kJ mol-1 (2.303RT)-1; for 4-(dimethylamino)-1-butyl acetate (4), log k1 (s-1) = (11.91 +/- 0.43) - (163.5 +/- 4.8) kJ mol-1 (2.303 RT)-1; for 4-oxo-1-pentyl acetate (7), log k1 (s-1) = (12.77 +/- 0.36) - (202.8 +/- 4.6) kJ mol-1 (2.303RT)-1.The presence of the (CH3)2N group in these acetates appears to provide anchimeric assistance in the elimination; methyl acetate and the corresponding heterocyclic products arise from an intimate ion-pair mechanism.The CH3CO substituent is believed to influence the pyrolysis rate of 5-acetoxy-2-pentanone by a weak steric acceleration.
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