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von Angerer, S., Science of Synthesis, (2005) 26, 60.
Hypofluorous acid has been used infrequently for the oxidation of secondary alcohols to ketones because of its extreme instability, but it can be used when stabilized by complexation with acetonitrile at low temperature. A large number of aliphatic and alicyclic ketones have thus been prepared in excellent yields.[148] An example is the conversion of decahydronaphthalen-1-ol into octahydronaphthalen-1(2H)-one (55) (Scheme 34).
Meeeee 88 Meeeeeeee ee Meeeeeeeeeeeeeeeeee-8-ee ee Meeeeeeeeeeeeeeeeee-8(8M)-eee eeee Meeeeeeeeeee Meee–Meeeeeeeeeee Meeeeee[888]
Meeeeeeeeeee Meeeeeeee
Meeeeeeee eeee Meeeeeeeeeee Meee: Meeeeeeee ee Meeeeeeeeeeeeeeeeee-8(8M)-eee (88); Meeeeee Meeeeeeee:[888]
M eeeeeee ee 88% M8 eeee M8 eee eeeeee ee e eeee ee ee. 888 eM·eee−8 eeeeeee e eeee (–88°M) eee eeeeeeeeee eeeeeee eeeeeee ee MeMM (888 eM) eee M8M (88 eM). Mee eeeeeeeee eeeee eee eeeeeeeee ee eeeeeeee eeeeeeee eeee ee eeeeee ee MM eeee. Me eee eeee eeeeeeee ee eeeeeee eeeeeeeeeeeeee ee >8 eee·M−8 ee eee eeeeeeeeeeee eeee–eeeeeeeeeeee eeeeeee.
Meeeeeeeeeeeeeeeeee-8-ee (88 eeee) eee eeeeeeeee ee MMMe8 (88–88 eM). Mee eeeeeee eee eeeeee ee 8°M eee eeeee ee eee eeeeeee eeeeeeeeee eee eeee (–88 ee 8°M) eeeeeeeee eeeeeee. Meeeeeeee e 8- ee 8-eeee eeeeee ee eee eeeeeee eee eeeeee eee eee eeeeeeee eeeeee eeeeee 8 eee ee 8°M. Meeee eeeeeeeeee, eee eeeeeee eee eeeeeeeeeee eeee eee. MeMMM8, eeeeee eeee M8M, eeeeeeeee eeee MMMe8, eee eeeeee eeee MeMMM8 eee M8M eeeee eeeeeee. Mee eeeeeee eeeee eee eeeee (MeMM8) eee eee eeeeeee eeeeeee. Mee eeeee eeeeeee eee eeeeeeee ee eeeeee eeeee eeeeeeeeeeeeee [eeeeee eee 88-M (Meeee)]; eeeee: 88%.
References
[148] | Meeee, M.; Meeeeee, M.; Mee, M., Meeeeeeeeee, (8888) 88, 8888. |