Photochemistry of 3-amino-1,2-benzisoxazole: unexpected photoisomerization of an amino-spiro-2H-azirine to a 1H-diazirine

Nunes C. M., Pinto S. M. V., Reva I., Fausto R.

TETRAHEDRON LETTERS, cilt.57, sa.46, ss.5038-5041, 2016 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 57 Sayı: 46
  • Basım Tarihi: 2016
  • Doi Numarası: 10.1016/j.tetlet.2016.09.098
  • Dergi Adı: TETRAHEDRON LETTERS
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.5038-5041
  • İstanbul Kültür Üniversitesi Adresli: Evet

Özet

UV irradiation of 3-amino-1,2-benzisoxazole isolated in an argon matrix leads to the formation of an amino-spiro-2H-azirine. The amino-spiro-2H-azirine was found to photoisomerize back to 3-amino1,2-benzisoxazole and also to a 1H-diazirine, which isomerizes to a carbodiimide. All the reported species were characterized experimentally by IR spectroscopy and confirmed by comparison with theoretical IR spectra. The discovery of the transformation of an amino-spiro-2H-azirine into a 1H-diazirine is unprecedented in the chemistry of reactive intermediates. (C) 2016 Elsevier Ltd. All rights reserved.