Solomon and Fryhle $11 th$ ed :

Most other benzene derivatives except phenols and tertiary aromatic amines do not undergo C- nitrosation reaction.

I agree that if there is a primary or secondary aromatic amine, the reaction will follow other routes but in case of other activating substituents EAS is the only route left for the electrophile $\ce{-^+N=O}$ for example with anisole.

Also it seems to contradict ron's answer

So which one is correct?

  • $\begingroup$ I don't see any contradiction. $\endgroup$
    – Mithoron
    Commented Mar 8, 2019 at 20:45

1 Answer 1


Anisole can be nitrosated in good yield reference here. This, and other references, note that the PhOMe group is unstable to the reaction conditions being cleaved to give phenol.

m-Xylene can be nitrosated in good yield, o-xylene and toluene in modest yield in TFA or sulfuric/acetic acid mix under nitric oxide reference here

Nitrosonium tetrafluoroborate will also nitrosate a range of electron-rich aromatics, including anisole and xylenes reference here

This suggests to me that the authors of the textbook quoted are in error, as two of the references predate the publication date of the textbook.


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