Abstract
The regioselective pyrolysis of sec-butyl methyl (trithio)carbonate was calculated at the MP2/6-31G(d) level in the Gaussian program. Twelve possible pathways were calculated. Nine of them gave the desired alkene products, 1-butene, E-butene, and Z-butene, and the other three, the rearrangement products, sec-butyl methyl ether and butanone for sec-butyl methyl carbonate and sec-butyl methyl thioether and butane-2-thione for sec-butyl methyl trithiocarbonate. It was shown that the two-step mechanism, including the carbonyl oxygen- or thion sulfur atom-involved six-membered ring transition state, as rate-determining step, is a preferred mechanism of the pyrolysis. The calculated product distribution is consistent with the experimental data on the pyrolysis of sec-butyl methyl carbonate. The product distribution for sec-butyl methyl trithiocarbonate was also predicted by the MP2/6-31G(d) method.
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