Navigation

0 Hits

  • Previous / Next

You are using Science Of Synthesis as a Guest.
Please login to access the full content or check if you have access via
31.22.1.1.1.1 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]

Meeeee 8 Meeeeeeeeee ee Meeeeeeeeeeee eeeee Meeeeeeeee Meeee Meeeeeeeee[‌88‌,‌88‌]

Meeeeeeeeee 8

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).

Meeeeeeeeeee Meeeeeeee

8-Meeeeeeeeee-8,8-eeeeeee 8-Meeee (88, M8=M; M8=Me); Meeeeee Meeeeeeee:[‌88‌]

M eeeeeee ee e-eeeeee (8.88e, 8.88eeee), eMe(MM8)8MMM (8.8eM, 8.88eeee) (MMMMMMM: eeeee) eee M8MM8 (8.88e, 8.88eeee) ee MMM (8eM) eee eeeeeee eee 8e ee ee, eee eeee eee 8e ee 88°M. Mee eeeeeee eee eeeeeeeee ee eee eeeeeeee ee 88% MMe, eeeeee ee eee eeeeeeeee eeee MeMMe. Meeeeeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, MM8Me8) eee eeeeeeeeee eeeeeeeeeeeeeeeee (MeMMe/eeeeee) eeee eee eeeee eeeeeeee ee eee-eeeee eeeeeee; eeeee: 8.88e (88%); ee 888888°M.

References


Cookie-Einstellungen