The Mistake in Carl Bosch's PhD Thesis: A Contribution to 'Retro-Chemistry'

The reaction of diethyl 1,3-acetonedicarboxylate and 2-bromoacetophenone described in Carl Bosch’s PhD thesis revealed a mistake concerning the structure of the isolated compound. A rework of the original showed that not the described cyclohexenone derivative was isolated, but a highly functionalized α,β-unsaturated cyclopenten­one derivative was formed. The structure was determined by spectroscopic methods and X-ray crystal structure analysis. In analogy to Bosch’s reaction, some new derivatives were synthesized.