Decarboxylation of endo- and exo-6-isobutyl-1,4-dimethyl-2,7-dioxabicyclo[2.2.1]heptane-6-carboxylic acids
Abstract
Decarboxylation of the title endo-acid (1) in chlorobenzene follows first-order kinetics with k= 3·7 × 10–4 s–1 at 69 °C and is significantly faster than decarboxylation of the corresponding exo-acid (2) with k= 7·8 × 10–5 s–1 at 121 °C; both (1) and (2) decarboxylate faster than a model compound, 2-methyl-1,3-dioxolan-2-acetic acid (5).