Generation and Characterization of a 4π-Electron Three-Membered Ring 1H-Diazirine: An Elusive Intermediate in Nitrile Imine-Carbodiimide Isomerization

Nunes C. M., Araujo-Andrade C., Fausto R., Reva I.

JOURNAL OF ORGANIC CHEMISTRY, cilt.79, sa.8, ss.3641-3646, 2014 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 79 Sayı: 8
  • Basım Tarihi: 2014
  • Doi Numarası: 10.1021/jo402744f
  • Dergi Adı: JOURNAL OF ORGANIC CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.3641-3646
  • İstanbul Kültür Üniversitesi Adresli: Evet

Özet

The photolysis at 222 nm of 5-methyltetrazole isolated in a cryogenic argon matrix leads to formation of methyl nitrile innine as primary product. Subsequent irradiation at 328 nm induces transformation of the nitrile imine into 4 pi-electron three-membered-ring 3-methyl-1H-diazirine, which photorearranges to give methyl carbodiimide. These products were characterized by IR spectroscopy and theoretical calculations. For the first time, a 1H-diazirine was captured as intermediate in the photoisomerization of nitrile imines into carbodiimides.