Why other benzene derivatives do not undergo nitrosation












2












$begingroup$


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?






organic-chemistry amines







share|improve this question











$endgroup$












  • $begingroup$
    I don't see any contradiction.
    $endgroup$
    – Mithoron
    2 days ago
















2












$begingroup$


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?






organic-chemistry amines







share|improve this question











$endgroup$












  • $begingroup$
    I don't see any contradiction.
    $endgroup$
    – Mithoron
    2 days ago














2












2








2





$begingroup$


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?






organic-chemistry amines







share|improve this question











$endgroup$




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?






organic-chemistry amines




organic-chemistry amines






share|improve this question















share|improve this question













share|improve this question




share|improve this question








edited 2 days ago









Avnish Kabaj

3,63831347




3,63831347










asked 2 days ago









StarboyStarboy

675




675












  • $begingroup$
    I don't see any contradiction.
    $endgroup$
    – Mithoron
    2 days ago


















  • $begingroup$
    I don't see any contradiction.
    $endgroup$
    – Mithoron
    2 days ago
















$begingroup$
I don't see any contradiction.
$endgroup$
– Mithoron
2 days ago




$begingroup$
I don't see any contradiction.
$endgroup$
– Mithoron
2 days ago










1 Answer
1






active

oldest

votes


















4












$begingroup$

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.






share|improve this answer











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    1 Answer
    1






    active

    oldest

    votes








    1 Answer
    1






    active

    oldest

    votes









    active

    oldest

    votes






    active

    oldest

    votes









    4












    $begingroup$

    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.






    share|improve this answer











    $endgroup$


















      4












      $begingroup$

      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.






      share|improve this answer











      $endgroup$
















        4












        4








        4





        $begingroup$

        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.






        share|improve this answer











        $endgroup$



        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.







        share|improve this answer














        share|improve this answer



        share|improve this answer








        edited 2 days ago

























        answered 2 days ago









        WaylanderWaylander

        6,53411424




        6,53411424






























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