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Pfau-Plattner Azulene Synthesis

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr493

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Pfau-Plattner Azulene Synthesis. Comprehensive Organic Name Reactions and Reagents. 493:2185–2187.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

The preparation of azulene from cyclopentenocycloheptanone by the application of the ring expansion protocol is a multistep preparation involving the decomposition of diazoacetic ester, addition of the resulting carbene to indane, rearrangement of cycloheptatriene, hydrolysis of ester, decarboxylation, and dehydrogenation is known as the Pfau–Plattner azulene synthesis. This reaction has been amended by the direct addition of carbene generated from diazomethane, to indane. This reaction has a limited use in organic synthesis, perticullarlly for the azulene derivatives.

Keywords:

  • carbenes;
  • diazoacetic ester;
  • cycloheptatriene;
  • azulene