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Synthesis 2015; 47(13): 1887-1892
DOI: 10.1055/s-0034-1380495
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© Georg Thieme Verlag Stuttgart · New York

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

Toni Smeilus
a   Institute of Organic Chemistry, University of Leipzig, Johannisallee 29, 04103 Leipzig, Germany
,
Lothar Hennig
a   Institute of Organic Chemistry, University of Leipzig, Johannisallee 29, 04103 Leipzig, Germany
,
Lothar Beyer
b   Institute of Inorganic Chemistry, University of Leipzig, Johannisallee 29, 04103 Leipzig, Germany   Email: giannis@chemie.uni-leipzig.de
,
Joachim Sieler
b   Institute of Inorganic Chemistry, University of Leipzig, Johannisallee 29, 04103 Leipzig, Germany   Email: giannis@chemie.uni-leipzig.de
,
Athanassios Giannis*
a   Institute of Organic Chemistry, University of Leipzig, Johannisallee 29, 04103 Leipzig, Germany
› Author Affiliations
Further Information

Publication History

Received: 12 February 2015

Accepted after revision: 02 March 2015

Publication Date:
30 March 2015 (online)

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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.

Key words

cyclization - condensation - amides - benzylation - esters

Supporting Information

    Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380495.
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