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Photochemistry of Tris(2,4-dibromophenyl)amine and its Application to Co-oxidation on Sulfides and Phosphines†
Photochemistry and Photobiology ( IF 2.6 ) Pub Date : 2021-02-20 , DOI: 10.1111/php.13403 Sergio M Bonesi 1, 2, 3 , Mariella Mella 4 , Daniele Merli 4 , Stefano Protti 3
Photochemistry and Photobiology ( IF 2.6 ) Pub Date : 2021-02-20 , DOI: 10.1111/php.13403 Sergio M Bonesi 1, 2, 3 , Mariella Mella 4 , Daniele Merli 4 , Stefano Protti 3
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The photochemistry of tris(2,4-dibromophenyl)amine was investigated via time-resolved nanosecond spectroscopy. The tris(2,4-dibromophenyl)amine radical cation (“Magic Green”) was immediately detected after the laser pulse; this intermediate then cyclizes to N-aryl-4a,4b-dihydrocarbazole radical cation. The latter transient reacted with molecular oxygen to provide the corresponding hydroperoxyl radical, which smoothly co-oxidize sulfides into sulfoxides. On the other hand, the photogenerated “Magic Green” was exploited to promote the co-oxidation of nucleophilic triarylphosphines to triarylphosphine oxides through an electron transfer process preventing the amine cyclization. In this case, the intermediate Ar3POO•+ was found to play a key role in phosphine oxide formation.
中文翻译：
三(2,4-二溴苯基)胺的光化学及其在硫化物和膦共氧化中的应用†
通过时间分辨纳秒光谱研究了三 (2,4-二溴苯基) 胺的光化学。激光脉冲后立即检测到三（2,4-二溴苯基）胺自由基阳离子（“魔术绿”）；该中间体然后环化为N-芳基-4a,4b-二氢咔唑自由基阳离子。后一瞬态与分子氧反应以提供相应的氢过氧自由基，其顺利地将硫化物共氧化成亚砜。另一方面，利用光生“魔法绿”通过防止胺环化的电子转移过程促进亲核三芳基膦共氧化为三芳基膦氧化物。在这种情况下，中间体 Ar 3 POO •+ 发现在氧化膦的形成中起关键作用。
更新日期：2021-02-20
中文翻译：
三(2,4-二溴苯基)胺的光化学及其在硫化物和膦共氧化中的应用†
通过时间分辨纳秒光谱研究了三 (2,4-二溴苯基) 胺的光化学。激光脉冲后立即检测到三（2,4-二溴苯基）胺自由基阳离子（“魔术绿”）；该中间体然后环化为N-芳基-4a,4b-二氢咔唑自由基阳离子。后一瞬态与分子氧反应以提供相应的氢过氧自由基，其顺利地将硫化物共氧化成亚砜。另一方面，利用光生“魔法绿”通过防止胺环化的电子转移过程促进亲核三芳基膦共氧化为三芳基膦氧化物。在这种情况下，中间体 Ar 3 POO •+ 发现在氧化膦的形成中起关键作用。
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