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Location effect of an OH group on the chemiluminescence efficiency of 4-hydroperoxy-2-(o-,m-, orp-hydroxyphenyl)-4,5-diphenyl-4H-isoimidazoles

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
46
Issue
11
Identifiers
DOI: 10.1016/j.tetlet.2005.01.084
Keywords
  • Chemiluminescence
  • Lophine Peroxide
  • Conical Intersection
  • Hydrogen Bond

Abstract

Graphical abstract The location effect of an OH group on the chemiluminescence efficiencies of 4-hydroperoxy-2-( o-, m-, or p-hydroxyphenyl)-4,5-diphenyl-4 H-isoimidazoles 4a , 4b , and 4c was investigated. The efficiency of 4a with o-OH was 0.28 times of that of lophine peroxide on the initiation with KOH/MeOH. When the trigger base was changed to TBAF/THF, the efficiency was 530-fold in a dry DMF. However, there is not such dramatic change in the efficiency for 4b with m-OH and 4c with p-OH by the change of trigger bases.

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