The 8-chlorobicyclo[3.2.1]oct-6-ene 3 has been prepared by a [3+2] cycloaddition route, and converted to the bicyclic a-methylene ketones 6 and 8-12, some of which showed cytotoxic properties.
Synthesis and properties of 1,1′-methylene-2,2′-dipyrrolyl ketone
✍ Scribed by J. A. de Groot; J. H. Koek; J. Lugtenburg
- Publisher
- Elsevier Science
- Year
- 2010
- Tongue
- English
- Weight
- 423 KB
- Volume
- 100
- Category
- Article
- ISSN
- 0165-0513
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✦ Synopsis
Abstract
1,1′‐methylene‐2,2′‐dipyrrolyl ketone can be conveniently prepared in high yield, starting from pyrrole, in three steps. It shows extreme properties that are not observed in comparable rigid ketone systems. These chemical and physical properties can be explained assuming mesomeric forms with charge separation resulting from the electron rich pyrrole rings and the rigidity of the system. The fluorescence quantum yield is 0.07 and the fluorescence lifetime is 27 ns.
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