Photochemical reactions of 1-oxo-2-diazo-1, 2-dihydronaphthalenes and reactivity of their products

K. Tanigaki, T. Honda, T. W. Ebbesen

Research output: Contribution to journalConference articlepeer-review

1 Citation (Scopus)


Photochemical reactions of 4-tolyl 1-oxo-2-diazo-1,2-dihydronaphthalene-5-sulfonate (DNQ-5STL) are studied, as a typical example of six-membered ring α -diazoketones, together with its two prototype molecules, i.e., 1-oxo-2-diazo-1,2-dihydrobenzene (DBQ), 1-oxo-2-diazo-1,2-dihydronaphthalene (DNQ), by reverse-phase liquid chromatography. The obtained products under different reaction conditions, such as photochemical reactions of pure solid DNQ-5STL in air and in vacuo, are examined. The reactivity of the carboxy compounds produced in air or in a water-containing solution is also discussed. They exhibit decarboxylation, dimerization or azo formation in the presence of bases, being markedly dependent on the type of molecules. The azo formation rate constant of the 3-carboxyindene analogue from DNQ-5STL is much greater than that of its dimerization.

Original languageEnglish
Pages (from-to)291-295
Number of pages5
JournalPolymeric Materials Science and Engineering, Proceedings of the ACS Division of Polymeric Materials Science and Engineering
Publication statusPublished - 1989 Dec 1
Externally publishedYes
EventProceedings of the ACS Division of Polymeric Materials: Science and Engineering - Miami Beach, FL, USA
Duration: 1989 Sep 111989 Sep 18

ASJC Scopus subject areas

  • Chemical Engineering (miscellaneous)
  • Polymers and Plastics


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