Abstract
3-Phenoxypropanoic acid (
1
), 3-(phenylthio)propanoic acid (
2
), and 4-phenylbutanoic acid (
3
) were pyrolysed between 520 and 682
K. Analysis of the pyrolysates showed the elimination products to be acrylic acid and the corresponding arene. Pyrolysis of ethyl 3-phenoxypropanoate (
4
) and its methyl analogue (
5
), ethyl 3-(phenylthio)propanoate (
6
) and its methyl counterpart (
7
), and 3-phenoxypropane nitrile (
8
) were also investigated between 617 and 737
K. The thermal gas-phase elimination kinetics and product analysis are compatible with a thermal retro-Michael reaction pathway involving a four-membered cyclic transition state.
Gas-phase elimination kinetics and product analysis lend support to a thermal retro-Michael reaction pathway involving cyclic transition states.