Synthesis and characterization of 2-chloro-3-benzylthiopyrrolo[1,2-a]- benzimidazol-1-one and 2,3-di(benzylthio)pyrrolo[1,2-a]benzimidazol-1-one.

Description:

The reaction between o-phenylenediamine and 2,3-dichloromaleic anhydride has been probed and found to give 2,3-dichloropyrrolo[1,2-a]- benzimidazol-1-one as the major product. Chlorine substitution in 2,3-dichloropyrrolo[1,2-a]benzimidazol-1-one by added benzylthiol occurs in the presence of pyridine to provide the corresponding monosulfide and disulfide derivatives. The first benzylthiol ligand undergoes reaction at the C-3 position of the five-membered pyrrolo-1-one ring, with the addition of the second benzylthiol ligand occurring at the remaining chlorine-substituted carbon. The mono- and disulfide derivatives have been isolated and characterized in solution by NMR, IR, and UV-vis spectroscopies, and the solid-state structure of 2,3-di(benzylthio)pyrrolo[1,2-a]benzimidazol-1-one has been established by X-ray crystallography.

Creator(s): Huang, Shih-Huang
Creation Date: December 2003
Partner(s):
UNT Libraries
Collection(s):
UNT Theses and Dissertations
Usage:
Total Uses: 280
Past 30 days: 5
Yesterday: 1
Creator (Author):
Publisher Info:
Publisher Name: University of North Texas
Place of Publication: Denton, Texas
Date(s):
  • Creation: December 2003
  • Digitized: November 17, 2003
Description:

The reaction between o-phenylenediamine and 2,3-dichloromaleic anhydride has been probed and found to give 2,3-dichloropyrrolo[1,2-a]- benzimidazol-1-one as the major product. Chlorine substitution in 2,3-dichloropyrrolo[1,2-a]benzimidazol-1-one by added benzylthiol occurs in the presence of pyridine to provide the corresponding monosulfide and disulfide derivatives. The first benzylthiol ligand undergoes reaction at the C-3 position of the five-membered pyrrolo-1-one ring, with the addition of the second benzylthiol ligand occurring at the remaining chlorine-substituted carbon. The mono- and disulfide derivatives have been isolated and characterized in solution by NMR, IR, and UV-vis spectroscopies, and the solid-state structure of 2,3-di(benzylthio)pyrrolo[1,2-a]benzimidazol-1-one has been established by X-ray crystallography.

Degree:
Level: Master's
Discipline: Chemistry
Language(s):
Subject(s):
Keyword(s): Chlorine | crystallography | chlorine substitution
Contributor(s):
Partner:
UNT Libraries
Collection:
UNT Theses and Dissertations
Identifier:
  • OCLC: 54479642 |
  • ARK: ark:/67531/metadc4415
Resource Type: Thesis or Dissertation
Format: Text
Rights:
Access: Public
License: Copyright
Holder: Huang, Shih-Huang
Statement: Copyright is held by the author, unless otherwise noted. All rights reserved.