Papers

Dec, 2012

SYNTHESIS OF BIS-NAPHTHOPORPHYRINS

HETEROCYCLES
  • Hiroki Uoyama
  • ,
  • Hiroko Yamada
  • ,
  • Tetsuo Okujima
  • ,
  • Hidemitsu Uno

Volume
86
Number
1
First page
515
Last page
534
Language
English
Publishing type
Research paper (scientific journal)
DOI
10.3987/COM-12-S(N)50
Publisher
PERGAMON-ELSEVIER SCIENCE LTD

Ethanonaphthoporphyrins with a halogen atom at the zeta position were prepared by the [3+1] porphyrin synthesis of halogen-substituted ethanobenz[f]isoindole with a tripyrrane derivative. The halogeno porphyrins were converted to the corresponding ethynyl and pinacolatoboronyl compounds by Sonogashira and borylation reactions, respectively. Suzuki, Sonogashira, and Glaser coupling reactions of these ethanonaphthoporphyrins gave bis-porphyrins connected with no atom, acetylene, and butadiyne, respectively. Retro Diels-Alder reaction of these bis-porphyrins brought about the conversion of bicyclo[2.2.2]octadiene (BCOD) to benzene moieties to give bis-naphthoporphyrins, quantitatively.

Link information
DOI
https://doi.org/10.3987/COM-12-S(N)50
Web of Science
https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=JSTA_CEL&SrcApp=J_Gate_JST&DestLinkType=FullRecord&KeyUT=WOS:000313766800039&DestApp=WOS_CPL
URL
http://www.scopus.com/inward/record.url?partnerID=HzOxMe3b&scp=84880607881&origin=inward
ID information
  • DOI : 10.3987/COM-12-S(N)50
  • ISSN : 0385-5414
  • SCOPUS ID : 84880607881
  • Web of Science ID : WOS:000313766800039

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