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31.22.1.3.1.4 Variation 4: Using 3-Chloroperoxybenzoic Acid

DOI: 10.1055/sos-SD-031-01513

Rück-Braun, K.; Priewisch, B.Science of Synthesis, (2007311343.

3-Chloroperoxybenzoic acid in dichloromethane or chloroform is also suited for the oxidation of substituted anilines 69 to nitrosobenzenes 70 (Scheme 35).[‌86‌‌88‌] The reactions are carried out by the dropwise addition of a solution of the oxidant to a solution of the substrate (or vice versa) at 0°C or below. Under essentially similar conditions, perbenzoic acid can also be used as an oxidizing agent for the preparation of nitrosobenzenes.[‌89‌,‌90‌]

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M8 M8 M8 Meeeeeeeee Meeeeeeeeeeee Meeee (%) ee (°M) Mee
Me e-Me Me MM8Me8, 8°M, 8e, ee, 88e M (MeMM) 88 888888 [‌88‌]
Me M Me MM8Me8, 8°M, 8eee MM 88 888888 (eee) [‌88‌]
Me M M MMMe8, 8°M ee eeeeee, 88eee MMM 88 888888 [‌88‌]
Me M Me MM8Me8, 8°M, 8e, ee, 88e M (MeMM) 88 888888 [‌88‌]

e M: eeeeeeeeeeeeeeeee; MM: eeeeee eeeeeeeeeeeeee; MMM: eeee-eeeee eeeeeeeeeeeeee.

Meeeeeee eeee ee 88 eee eeee ee eeeeeeeee eeee eeeeeeeeeeee (eeeeeeeeeeeeeeeeeeeee)eeeeeeeeeeeee (e.e., 88) ee eeeeeeeee eeee eeeeeeee eeeeeee eee M-eeeeeeeeeeeeeeeee; eeeee eeeeeeeeeeeee eee eeee eeeeeeee ee 8-eeeeeeeeeeeeeeeeeee ee eeeeee eeeeeeeeeeeeeee eeee ee 88 (Meeeee 88).[‌88‌,‌88‌] Me eeeeeeee, eeee eeeeee eee ee eeeeeeee ee eeeeeeeeee eeeeeee eeeeeeeeeeee eeeeeeee eeeeeeeeeeee.[‌88‌]

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8,8-Meeeeee-8-eeee-eeeee-8-eeeeeeeeeeeeee (88, M8=M8=Me; M8=e-Me):[‌88‌]

M eeee ee 8,8-eeeeeee-8-eeee-eeeeeeeeeeee (88, M8=M8=Me; M8=e-Me; 8.8e, 88.8eeee) ee eeeee MM8Me8 (88eM) eee eeeee eeeeeeee ee e eeee ee MMMMM (88% eeeeee, 8.88e, 88eeee) ee eeeee MM8Me8 (888eM) ee ee eee eeee. Mee eeeeeee eee eeeeeee ee 8°M eee 8e eee eeeeeeeeee ee ee eeeeeeeee. Meee eee, ee eee eeeeee ee eeee eeee 88% ee Me8MM8 (8×888eM) eee M8M (888eM), eeeeee eee eeeeeee eeeee eee eeeee (Me8MM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Meeeeeeeeeeeeeeee (MeMM) ee eee eeeeeee eeee e eeeeee eeeeeeeeeee eeeee; eeeee: 8.8e (88%); ee 888888°M.

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