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- W2008415025 abstract "Mechanistic studies on the photochemical reactions of benzfurazan. From other works it is known that irradiation of benzfurazan (1) in methanol gives the carbaminacid-ester 4, whereas in benzene the azepinederivative 3 is obtained (Scheme 1). The compounds 5–8 (Scheme 2) have been proposed as intermediates. In our investigations we detected and characterized by means of UV.- and IR.-spectroscopy the two species 5 and 8. Irradiation of 1 with 350 nm light at room temperature in a strongly polar solvent (e.g. H2O) yields exclusively 5 (Fig. 1) with a quantum yield of 0.48. In non polar solvents (e.g. hexane) 5 isomerizes in a second photochemical step to 8 (quantum yield 0.43) (Fig. 3). Thermally, 5 can be converted back to 1. The rate constant for this reaction at room temperature is 2 · 10–5s–1. The transformation 5 → 8 was also investigated at low temperature. There was no direct evidence for any intermediates of the type oxazirene (6) or nitrene (7). However, the formation of azepine 3 upon irradiation of 5 in benzene suggests as intermediate the nitrene 7 which could be converted into 8 in a fast thermal reaction (Scheme 3)." @default.
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- W2008415025 date "1976-12-15" @default.
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- W2008415025 title "Zum Mechanismus der Photochemie des Benzfurazans" @default.
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- W2008415025 doi "https://doi.org/10.1002/hlca.19760590812" @default.
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