First intramolecular benzyne Diels-Alder reaction with an acyclic diene. Unusual effect of diene geometry on the course of the reaction

Article abstract of DOI:10.1016/0040-4039(95)01980-V

The first intramolecular benzyne Diels-Alder reaction with an acyclic diene is reported. The course of the reaction is dependent on the diene geometry. Trans dienes afforded [4+2] cycloadducts; cis dienes apparently give [2+2] cycloadducts followed by further rearrangement, a mechanistic course which is supported by deuterium labeling experiments.