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Photochemistry of 3-amino-1,2-benzisoxazole: unexpected photoisomerization of an amino-spiro-2H-azirine to a 1H-diazirine
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.
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Reference:
Benzisoxazole – Wikipedia,
,Benzisoxazole – an overview | ScienceDirect Topics