Solid-state and solution photolyses of tetracyanobenzene with benzyl cyanides or benzyl alcohols

Yoshikatsu Ito, Hironari Nakabayashi, Shigeru Ohba, Hiroyuki Hosomi

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9 Citations (Scopus)

Abstract

Intermolecular photoreactions of tetracyanobenzene (TCNB) with benzyl cyanide (BzCN), benzyl alcohol (BzOH) and various others were investigated in the solid state (cocrystal) and in solution. The new solid-state photocoupling reaction found for the cocrystal TCNB·BzCN, giving a stilbene derivative followed by the solution isomerization into an isoindole derivative, is a very limited reaction. On the other hand, its solution photocondensation to give products of the diphenylmethane type occurred quite generally, probably under acidic conditions. (C) 2000 Elsevier Science Ltd.

Original languageEnglish
Pages (from-to)7139-7152
Number of pages14
JournalTetrahedron
Volume56
Issue number37
Publication statusPublished - 2000 Sep 8

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Keywords

  • Crystalline complexes
  • Cyano compounds
  • Electron transfer
  • Photochemistry

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Ito, Y., Nakabayashi, H., Ohba, S., & Hosomi, H. (2000). Solid-state and solution photolyses of tetracyanobenzene with benzyl cyanides or benzyl alcohols. Tetrahedron, 56(37), 7139-7152.