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25.6.2.2.10 Variation 10: Additional Procedures

DOI: 10.1055/sos-SD-025-00388

Ditrich, K.Science of Synthesis, (200725548.

Fétizon's reagent, silver carbonate on Celite,[‌71‌] is a valuable reagent for the oxidation of alcohols to aldehydes, e.g. 51, and in particular for alcohols that contain acid- and/or base-sensitive functionalities (Scheme 23). The reactions almost always occur smoothly in high yields. Overoxidation or side reactions are uncommon; hetarenecarbaldehydes, e.g. 52 and 53, which are otherwise inaccessible, can be prepared starting from the corresponding hetarylmethanols.[‌72‌] Unfortunately, the precious reagent has to be used in a large excess; consequently, the method is predominantly useful for small-scale preparations.

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Meeeee 88 Meeeeee-Meeeeeee Meeeeeeee ee Meeeeeeeeeeee eeee Meeeee[‌88‌]

M eeeeeeeee-eeeeeeeee eeeeeee eee eee eeeeeeeee ee eeeeeeeeeeeee 88 ee eee eeeeeeeeeeeee eeeeeeeeeeeeeeeeee 88 eee eeee eeeeeeee (Meeeee 88).[‌88‌] Me eeeeeeee eeeeee eeee ee ee eeeeeee ee eeeeeeeeeeeeee eeeeeee. Meee eeeeeeeee eeeeee eeeeeeeeeeee eeeeee eeee ee eee eeeeeeeeeeee eeee eee ee eeeeeeeeee ee eee eeeeeeeee ee eeeee- ee eeeeeee-eeeeeeeeeee eeeeeeeeeeeeeeeeee. Meeeeeeeeeeeeeee eee eeeeeeeee ee eeee eeeeee eeeeee; eeeee ee eeee eeeeeeeee eeee ee eeeeeeeee, eeeeeeee-eeee eeeeeeeeee eee eeee eeeeeeeee. Mee eeeeeeeee eeeeeeee ee eeeeee eeeeeeee ee eeeeeeeeee eee eeeeeeee eeeeeee eeee eeeee eee eeeeeeeeeee eee eeeeeee eeeeee; ee eeee eeeeeeeeee eeeeee, ee eeee ee eeeeeeee eee eeeeeeee.

Meeeee 88 Meeeeeeee ee Meeeeeeeeeeee eeee Meeeee Meee, Meeeeeeee ee Meeeeeeee(MMM) Meeeeeeeeeeeeeeeeeeeeeeee[‌88‌]

Meeeeeeeeee 88

Me8 Meeee (%) Mee
8-MM8M8 88 [‌88‌]
8-Mee 88 [‌88‌]
8,8-M8M8M8 88 [‌88‌]
8-M8MM8M8 88 [‌88‌]
8-M8MM8M8 88 [‌88‌]
8-MeM8MM8M8 88 [‌88‌]

Meeeeeeeeeee Meeeeeeee

8-Meeeeeeeeeeeeeeeeee (88); Meeeeee Meeeeeeee ee Méeeeee Meeeeeeee:[‌88‌]

Meeeee eee eeeeeeee ee eeeeeeeeeeee eeeeeee eeee MeMM eeeeeeeeee 88% ee MMe eee eeee eeee M8M eeeee eee eeeeeeeee eeee eeeeeee eee eeee eeee eeeeeeee eeee. Mee eeeee eee eeee eeeee eeeee eeeeeee eeeeeeee ee 888°M. Mee eeeeeeee Meeeee (88e) eee eeeee ee e eeeeeee eeee ee MeMM8 (88e, 888eeee) ee M8M (888eM). Me8MM888M8M (88e, 888eeee) eeeeeeeee ee M8M (888eM) eee eeeeee eeeee ee eee eeeeeeeeee; eeee eeeeeeee eeeeeeee, eeeeeeee eee eeeeeeeee eee eeeeeee 88eee. Mee eeeeee-eeeee eeeeeeeeeee eee eeeeeeeee ee eeeeeeeeee eee eeeee eeeee eeeeeee eeeeeeee. Meeeeeee eeeeee ee M8M eeee eeeeeee ee eeeeeeeeee eeeeee eeee eeeeeee (MMMMMMM: eeeeeeeeee). Mee eeeeeee eeeeee ee eeeeeeee eeeeeeeee 8eeee ee Me8MM8 eee 8.88e ee eee eeeee.

(8-Meeeeeeeeeeee)eeeeeeee (888ee, 8eeee) eee eeeee ee e eeeeeeeeee ee eeeeeeeeeeeeee eeeee Me8MM8/Meeeee [8.88e eeeeeee eeeeeeeeee Me8MM8 (8.8e, 8eeee)] ee MM8Me8 (88eM). Mee eeeeeee eee eeeeeeee eee 8e. Meee eeeeeee ee ee, eee eeeee eee eeeeeee ee eeeeeeeeee eee eeeeee eeee MM8Me8 (88eM). Mee eeeeeeee eeeeeeeee eeee eeeeeeeeeeee eeeee eeeeeee eeeeeeee; eeeee: 88% (eeeeeeee eee eeeeeeeeeeeee ee eee 8,8-eeeeeeeeeeeeeeeeeeeeee; ee 888°M).

8-Meeeeeeeeeeeeeeeeee (88, M8=M8=M; M8=MM); Meeeeee Meeeeeeee ee 8,8-Meeeeeee-8,8-eeeeeeeeeeee-8,8-eeeeeee Meeeeeeee:[‌88‌]

MMM (888ee, 8eeee) eee eeeee ee e eeee ee (8-eeeeeeeeeeeee)eeeeeeee (88, M8=M8=M; M8=MM; 888ee, 8eeee) ee 8,8-eeeeeee (88eM). Me ee eeeeeeeeee eeeeeeee, eee eeeeeee eeeeeeeeeee eeeeee eeee eeeee eee 8,8-eeeeeeee-8,8-eeeeeee-8,8-eeeeeeeeeeeeeeee (MMMM8) eeeeeee ee eeeeeeeeeee. Meeee 88e, MMM eeeeeeeee eeeeeeee eeeeeeeeee ee eee eeeeeeee eeeeeeee. Mee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeeeee eee eeeeeee eeee MM8Me8. Mee eeeeeeeeeee MMMM8 eee eeeeeee ee eeeeeeeeee eee eee eeeeeeee eee eeeeeeeeeeee ee eeeeeee e eeeee eeeeeee, eeeee eee eeeeeeeeeeeeee (M8M); eeeee: 888ee (88%); ee 888888°M.

8-Meeeeeeeeeeeeeeee (88, Me8=8-M8MM8M8); Meeeeee Meeeeeeee:[‌88‌]

Me e eeee ee (8-eeeeeeeeeee)eeeeeeee (88, Me8=8-M8MM8M8; 8.88e, 88eeee) ee 8,8-eeeeeeeeeeeeee (88eM), Me(MMe)8 (8.88e, 8eeee) eee eeeee. Me 88% MMM8 (e=8.88e·eM; 8.88e, 88eeee) eee eeeeeeeeee ee 88°M eee eee eeeeeee eee eeeeeeee eee 88e. Mee eeeeeee eee eeeeeee ee eeee ee ee eee eeee eeeeeee eeee M8M (88eM). Mee eeeeee eeee eeeeeeeee eee eee eeeeeee eeeee eee eeeeeeeee eeee 8,8-eeeeeeeeeeeeee (8×88eM). Mee eeeeeeee eeeeeeee eeee eeeee (MeMM8), eee eeeeeee eee eeeeeeeeee eeeee eeeeeee eeeeeeee, eee eee eeeeeeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee; eeeee: 8.88e (88%); ee 888888°M.

References