Abstract
AbstractThe gas phase elimination of 4‐(methylthio)‐1‐butyl acetate and 1‐chloro‐4‐(methylthio)‐butane has been investigated in a seasoned, static reaction vessel over the temperature range of 310–410°C and the pressure range of 46–193 Torr. The presence of the inhibitors propene, cyclohexene, and/or toluene had no effect on the rates. The reactions are homogeneous, unimolecular, and obey a first‐order rate law. The rate coefficients are given by the following Arrhenius equations: for 4‐(methylthio)‐1‐butyl acetate, log k1(s−1) = (12.32 ± 0.29) − (192.1 ± 3.6) kJ/mol/2.303RT; for 1‐chloro‐4‐(methylthio)‐butane, log k1(s−1) = (12.23 ± 0.59) − (175.7 ± 6.8) kJ/mol/2.303RT. The CH3S substituent in 1‐chloro‐4‐(methylthio)‐butane has been found to participate in the elimination reaction, where tetrahydrothiophene and methyl chloride formation may result from an intimate ion‐pair type of mechanism. The yield of a cyclic product in gas phase reactions provides additional evidence of an intimate ion pair mechanism through neighboring group participation in gas phase elimination of special types of organic halides.
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