The Release of Singlet Oxygen in the Reaction of Dioxiranes with Amine N-Oxides

✍ Scribed by Marta Ferrer; Francisco Sánchez-Baeza; Angel Messeguer; Waldemar Adam; Dieter Golsch; Felix Görth; Wolfgang Kiefer; Volker Nagel

• Publisher: John Wiley and Sons
• Year: 1998
• Tongue: English
• Weight: 150 KB
• Volume: 1998
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/(sici)1099-0690(199811)1998:11<2527::aid-ejoc2527>3.0.co;2-4

✦ Synopsis

The reactivity of dimethyldioxirane and methyl(trifluoro-luminescence and by chemical trapping with 9,10-dimethylanthracene. The nucleophilicity of the N-oxide determines methyl)dioxirane towards the amine N-oxides 1a-13a and ammonium derivatives 13b-d has been investigated. In the the efficacy of the 1 O 2 release in the deoxygenation. Thus, for the less nucleophilic heteroaromatic N-oxides, the dioxirane oxidation of the tertiary amines and nitrogen heteroarenes, the expected N-oxides are not always formed.

deoxygenation of the amine oxide competes ineffectively with the oxidation of the amine. The ammonium derivatives Instead, the in situ generated N-oxides are deoxygenated by the dioxirane with the release of singlet oxygen ( 1 O 2 ) at 13b-d do not promote the decomposition of the dioxiranes; as expected, they are epoxidized. comparable or even higher rates than the amine oxidation. The amount of 1 O 2 has been quantified by IR chemi-