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The photochemistry of beta-naphthoyl azide and 4-acetylphenoxycarbonyl azide: The chemical and physical properties of acylnitrenes
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The photochemistry of beta-naphthoyl azide and 4-acetylphenoxycarbonyl azide: The chemical and physical properties of acylnitrenes
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The photochemistry of beta-naphthoyl azide and 4-acetylphenoxycarbonyl azide: The chemical and physical properties of acylnitrenes
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Dissertation
The photochemistry of beta-naphthoyl azide and 4-acetylphenoxycarbonyl azide: The chemical and physical properties of acylnitrenes
1987
Overview
We have examined the chemical and physical properties of two acylnitrenes, 4-acetylphenoxycarbonylnitrene (APN) and $\\beta$-naphthoylnitrene (BNN) generated by the photolysis of 4-acetylphenoxycarbonyl azide and $\\beta$-naphthoyl azide (BNA) respectively. These nitrenes were investigated using low-temperature optical, electron spin resonance, and transient absorption spectroscopy as well as by traditional chemical trapping techniques. APN is a ground state triplet nitrene which appears to be no more than 5 kcal/mol below the lowest energy singlet nitrene. The properties of APN are dominated by those typically associated with triplet nitrenes: nonstereospecific addition to olefins and a readily detectable electron spin resonance spectrum. BNN is the first bona fide example of an acylnitrene with a singlet ground state. The properties of BNN are those typically associated with singlet nitrenes: direct or triplet sensitized irradiation of BNA gives products derived exclusively from the singlet nitrene.
