Abstract
AbstractIt is shown that dimethyl 5, 6, 8, 10‐tetramethyl‐ (3) and 8‐ (tert‐butyl)‐5,6,10‐trimethylheptalene‐1, 2‐dicarboxylate (5), and their derivatives rearrange reversibly on irradiation or on heating to yield the corresponding 1,6,8,10‐tetramethyl‐ (4) and 8‐(tert‐butyl)‐1,6,10‐trimethylheptalene‐1,2‐dicarboxylate (6), and their derivatives by double‐bond shift (π‐skeletal rearrangement) via a transition state with D2 symmetry as the highest possible one. This follows from the fact that (−)‐(P)‐3 is photochemically as well as thermally rearranged to give (−)‐(P)‐4 i.e. the π‐skeletal rearrangement occurs with retention of configuration of the heptalene skeleton and without loss of optical purity.
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