Does aniline react with diazonium ions at C or N?












3














Reaction of aniline with benzenediazonium cation



In the azo coupling of aniline with benzenediazonium cation, I thought of two possible products 1 and 2 that could be formed. However, I can't work out which will be preferred. What would be the major product and why?






organic-chemistry aromatic-compounds amines regioselectivity







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  • Are you aware of the mechanism of the diazo coupling reaction?
    – YUSUF HASAN
    4 hours ago










  • Anyhow... Have a look at this
    – YUSUF HASAN
    4 hours ago










  • Can't realise how it helps??
    – Aditya Garg
    3 hours ago
















3














Reaction of aniline with benzenediazonium cation



In the azo coupling of aniline with benzenediazonium cation, I thought of two possible products 1 and 2 that could be formed. However, I can't work out which will be preferred. What would be the major product and why?






organic-chemistry aromatic-compounds amines regioselectivity







share|improve this question
























  • Are you aware of the mechanism of the diazo coupling reaction?
    – YUSUF HASAN
    4 hours ago










  • Anyhow... Have a look at this
    – YUSUF HASAN
    4 hours ago










  • Can't realise how it helps??
    – Aditya Garg
    3 hours ago














3












3








3


1





Reaction of aniline with benzenediazonium cation



In the azo coupling of aniline with benzenediazonium cation, I thought of two possible products 1 and 2 that could be formed. However, I can't work out which will be preferred. What would be the major product and why?






organic-chemistry aromatic-compounds amines regioselectivity







share|improve this question















Reaction of aniline with benzenediazonium cation



In the azo coupling of aniline with benzenediazonium cation, I thought of two possible products 1 and 2 that could be formed. However, I can't work out which will be preferred. What would be the major product and why?






organic-chemistry aromatic-compounds amines regioselectivity




organic-chemistry aromatic-compounds amines regioselectivity






share|improve this question















share|improve this question













share|improve this question




share|improve this question








edited 8 mins ago









orthocresol♦

38.1k7112229




38.1k7112229










asked 4 hours ago









Aditya Garg

1343




1343












  • Are you aware of the mechanism of the diazo coupling reaction?
    – YUSUF HASAN
    4 hours ago










  • Anyhow... Have a look at this
    – YUSUF HASAN
    4 hours ago










  • Can't realise how it helps??
    – Aditya Garg
    3 hours ago


















  • Are you aware of the mechanism of the diazo coupling reaction?
    – YUSUF HASAN
    4 hours ago










  • Anyhow... Have a look at this
    – YUSUF HASAN
    4 hours ago










  • Can't realise how it helps??
    – Aditya Garg
    3 hours ago
















Are you aware of the mechanism of the diazo coupling reaction?
– YUSUF HASAN
4 hours ago




Are you aware of the mechanism of the diazo coupling reaction?
– YUSUF HASAN
4 hours ago












Anyhow... Have a look at this
– YUSUF HASAN
4 hours ago




Anyhow... Have a look at this
– YUSUF HASAN
4 hours ago












Can't realise how it helps??
– Aditya Garg
3 hours ago




Can't realise how it helps??
– Aditya Garg
3 hours ago










1 Answer
1






active

oldest

votes


















5














This is a really interesting question and the answer is that the reaction of benzenediazonium chloride with aniline is a bit different to most of the reactions of benzenediazonium salts in that the initial product is compound 1, diazoaminobenzene. It is possible to run the reaction to isolate diazoaminobenzene (prep here).



These diazoaminobenzene compounds are unstable with respect to reversion to a diazonium salt + nucleophile, and so many references suggest that the bottom product (4-aminoazobenzene) is directly produced. The procedure for the transformation of the diazaminobenzene to 4-aminoazobenzene is by heating to 50 °C with aniline (prep here).






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    1 Answer
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    1 Answer
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    active

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    active

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    active

    oldest

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    This is a really interesting question and the answer is that the reaction of benzenediazonium chloride with aniline is a bit different to most of the reactions of benzenediazonium salts in that the initial product is compound 1, diazoaminobenzene. It is possible to run the reaction to isolate diazoaminobenzene (prep here).



    These diazoaminobenzene compounds are unstable with respect to reversion to a diazonium salt + nucleophile, and so many references suggest that the bottom product (4-aminoazobenzene) is directly produced. The procedure for the transformation of the diazaminobenzene to 4-aminoazobenzene is by heating to 50 °C with aniline (prep here).






    share|improve this answer




























      5














      This is a really interesting question and the answer is that the reaction of benzenediazonium chloride with aniline is a bit different to most of the reactions of benzenediazonium salts in that the initial product is compound 1, diazoaminobenzene. It is possible to run the reaction to isolate diazoaminobenzene (prep here).



      These diazoaminobenzene compounds are unstable with respect to reversion to a diazonium salt + nucleophile, and so many references suggest that the bottom product (4-aminoazobenzene) is directly produced. The procedure for the transformation of the diazaminobenzene to 4-aminoazobenzene is by heating to 50 °C with aniline (prep here).






      share|improve this answer


























        5












        5








        5






        This is a really interesting question and the answer is that the reaction of benzenediazonium chloride with aniline is a bit different to most of the reactions of benzenediazonium salts in that the initial product is compound 1, diazoaminobenzene. It is possible to run the reaction to isolate diazoaminobenzene (prep here).



        These diazoaminobenzene compounds are unstable with respect to reversion to a diazonium salt + nucleophile, and so many references suggest that the bottom product (4-aminoazobenzene) is directly produced. The procedure for the transformation of the diazaminobenzene to 4-aminoazobenzene is by heating to 50 °C with aniline (prep here).






        share|improve this answer














        This is a really interesting question and the answer is that the reaction of benzenediazonium chloride with aniline is a bit different to most of the reactions of benzenediazonium salts in that the initial product is compound 1, diazoaminobenzene. It is possible to run the reaction to isolate diazoaminobenzene (prep here).



        These diazoaminobenzene compounds are unstable with respect to reversion to a diazonium salt + nucleophile, and so many references suggest that the bottom product (4-aminoazobenzene) is directly produced. The procedure for the transformation of the diazaminobenzene to 4-aminoazobenzene is by heating to 50 °C with aniline (prep here).







        share|improve this answer














        share|improve this answer



        share|improve this answer








        edited 8 mins ago









        orthocresol♦

        38.1k7112229




        38.1k7112229










        answered 3 hours ago









        Waylander

        5,80711021




        5,80711021






























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