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Schuster, Gary B. Autrey, Tom 2015-05-13T15:37:28Z 2015-05-13T15:37:28Z 10000-01-01 1987 1987 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. Made available in DSpace on 2015-05-13T15:37:28Z (GMT). No. of bitstreams: 2 license.txt: 4848 bytes, checksum: 96035ab3f5e1c23cc7138a224ce498bd (MD5) 8815317.PDF: 3431113 bytes, checksum: eedaeadcd924e0c7f8979a3e62316230 (MD5) Previous issue date: 1987 Embargo set by: Seth Robbins for item 78469 Lift date: Forever Reason: Restricted to the U of I community idenfinitely during batch ingest of legacy ETDs Restricted to the U of I community idenfinitely during batch ingest of legacy ETDs U of I Only 117 p. Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 1987. http://hdl.handle.net/2142/77258 (UMI)AAI8815317 eng Chemistry, Organic The Photochemistry of Beta-Naphthoyl Azide and 4-Acetylphenoxycarbonyl Azide: The Chemical and Physical Properties of Acylnitrenes text Ph.D. Chemistry Chemistry University of Illinois at Urbana-Champaign Dissertation