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

被引：6
|
作者：
Nunes, Claudio M. [1 ]
Pinto, Sandra M. V. [1 ]
Reva, Igor [1 ]
Fausto, Rui [1 ]
机构：
[1] Univ Coimbra, Dept Chem, CQC, P-3004335 Coimbra, Portugal
来源：
TETRAHEDRON LETTERS | 2016年 / 57卷 / 46期
关键词：
Benzisoxazole; Matrix isolation; Photochemistry; DFT calculations; Reactive intermediates; LOW-TEMPERATURE MATRIX; INTERMEDIATE; PYROLYSIS; BENZISOXAZOLES; ISOMERIZATION; REARRANGEMENT; CARBODIIMIDES; ISOXAZOLES; PHOTOLYSIS; AZIRINES;
D O I：
10.1016/j.tetlet.2016.09.098
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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.
引用
收藏
页码：5038 / 5041
页数：4
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