Regioselective and stereospecific synthesis, crystal structure and NMR assignments of N-[(Z)-1-oxo-1,3-diphenylprop-2-en-2-yl]-4-nitrobenzamide

Heshmat Allah Samimi, Bohari Mohd. Yamin

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

Isomerisation of cis and trans N-acyl-2-benzoyl-3-phenylaziridines to the corresponding N-(E ) and N-[(Z )-1-oxo-1-aryl-3- phenylprop-2-en-2-yl]-4- benzamide, respectively, in the presence of diethyl thiourea is described. The structure of N-[(Z )-1-oxo- 1-phenyl-3-phenylprop-2-en-2-yl]-4-nitrobenzamide is also confirmed by the single crystal X-ray diffraction study. A mechanism for this regiospecific rearrangement is proposed.

Original languageEnglish
Pages (from-to)358-361
Number of pages4
JournalJournal of Chemical Research
Volume38
Issue number6
DOIs
Publication statusPublished - 2014

Fingerprint

Thiourea
Isomerization
Crystal structure
Nuclear magnetic resonance
Single crystals
X ray diffraction
benzamide

Keywords

  • Ketoaziridine
  • Regio-controlled
  • Ring expansion
  • Stereospecific rearrangement

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Regioselective and stereospecific synthesis, crystal structure and NMR assignments of N-[(Z)-1-oxo-1,3-diphenylprop-2-en-2-yl]-4-nitrobenzamide. / Samimi, Heshmat Allah; Mohd. Yamin, Bohari.

In: Journal of Chemical Research, Vol. 38, No. 6, 2014, p. 358-361.

Research output: Contribution to journalArticle

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AB - Isomerisation of cis and trans N-acyl-2-benzoyl-3-phenylaziridines to the corresponding N-(E ) and N-[(Z )-1-oxo-1-aryl-3- phenylprop-2-en-2-yl]-4- benzamide, respectively, in the presence of diethyl thiourea is described. The structure of N-[(Z )-1-oxo- 1-phenyl-3-phenylprop-2-en-2-yl]-4-nitrobenzamide is also confirmed by the single crystal X-ray diffraction study. A mechanism for this regiospecific rearrangement is proposed.

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