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23.14.1.1.5.2 Variation 2: Photolysis of Cyclohexanones

DOI: 10.1055/sos-SD-023-00535

Tidwell, T. T.Science of Synthesis, (200623582.

The photolysis of cycloalkanones in solution gives mixtures of ketenes, aldehydes, and other products.[‌63‌,‌66‌‌70‌] Photolysis of cyclohexanone in water gives butylketene (41), which can be observed by UV spectroscopy for the measurement of its hydration kinetics.[‌34‌] This reaction occurs by a Norrish type I cleavage to form the diradical 73, which undergoes intramolecular hydrogen-atom transfer. For photolysis in methanol, the ester makes up 38% of the photoproducts together with some hex-5-enal (Scheme 22).[‌68‌]

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