Synthesis, spectroscopy, and reactivity of meso-unsubstituted azuliporphyrins and their heteroanalogues. Oxidative ring contractions to carba-, oxacarba-, thiacarba-, and selenacarbaporphyrins.

@article{Lash2004SynthesisSA,
  title={Synthesis, spectroscopy, and reactivity of meso-unsubstituted azuliporphyrins and their heteroanalogues. Oxidative ring contractions to carba-, oxacarba-, thiacarba-, and selenacarbaporphyrins.},
  author={T. D. Lash and D. A. Colby and S. Graham and S. Chaney},
  journal={The Journal of organic chemistry},
  year={2004},
  volume={69 25},
  pages={
          8851-64
        }
}
This paper reports the first detailed study on meso-unsubstituted azuliporphyrins, an important family of porphyrin-like molecules where one of the usual pyrrole rings has been replaced by an azulene subunit. Although the azulene moiety introduces an element of cross-conjugation, zwitterionic resonance contributors with tropylium and carbaporphyrin substructures give azuliporphyrins diatropic character that falls midway between true carbaporphyrins and nonaromatic benziporphyrins. Protonation… Expand
46 Citations
Synthesis, structural characterization and reactivity of heteroazuliporphyrins.
Out of the Blue! Azuliporphyrins and Related Carbaporphyrinoid Systems.
  • T. D. Lash
  • Chemistry, Medicine
  • Accounts of chemical research
  • 2016
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