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Please login to access the full content or check if you have access via Variation 1: Nitrosation of Phenols by Alkyl Nitrites

DOI: 10.1055/sos-SD-031-01513

Rück-Braun, K.; Priewisch, B.Science of Synthesis, (2007311325.

Phenols can be nitrosated by reaction with alkyl nitrite in an aqueous or aqueous alcoholic solution of a base, such as sodium hydroxide. Under the basic conditions a phenolic anion is the reactive species,[‌22‌] so that even phenols bearing deactivating groups can be nitrosated. 3-Methylbutyl nitrite (isoamyl nitrite) in dimethylformamide, containing potassium carbonate, can be used for the nitrosation of substituted phenols, naphthols, and their heterocyclic analogues to the corresponding benzo-1,4-quinone oximes 12 under nonaqueous conditions (Scheme 9).[‌22‌,‌23‌]

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M8 M8 Meeeeeeeee Meeee (%) ee (°M) Mee
M M eMe(MM8)8MMM (8.8 eeeee), ee, 88e 88 888888 [‌88‌]
MMM M eMe(MM8)8MMM (8.8 eeeee), 88°M, 88e 88 888888 [‌88‌]
M=MMMM=MM eMe(MM8)8MMM (8.8 eeeee), 88°M, 8e 88 >888 [‌88‌]
M Me eMe(MM8)8MMM (8.8 eeeee), ee ee 88°M, 8e 88 888888 [‌88‌]
Me M eMe(MM8)8MMM (8.8 eeeee), ee, 88e 88 888888 [‌88‌]
(MM=MM)8 eMe(MM8)8MMM, ee 88e 888888 [‌88‌]
MM(Me)=MM eMe(MM8)8MMM (8.8 eeeee), 8e, ee 88 888888 (eee) [‌88‌]
MM8Me M eMe(MM8)8MMM (8.8 eeeee), 88°M, 88e 88 8888 [‌88‌]

e Me eeeeeeee, 8-eeeeeee-8-eeeeeeee eee eeeeeeee ee 88% eeeee (ee 888888°M).

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