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Synthesis 2015; 47(13): 1887-1892
DOI: 10.1055/s-0034-1380495
DOI: 10.1055/s-0034-1380495
paper
The Mistake in Carl Bosch’s PhD Thesis: A Contribution to ‘Retro-Chemistry’
Further Information
Publication History
Received: 12 February 2015
Accepted after revision: 02 March 2015
Publication Date:
30 March 2015 (online)
Abstract
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.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380495.
- Supporting Information
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References
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