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Mechanism for reaction of NOCl (Tilden reagent) with primary amines
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Marty Silvia
Mechanism for reaction of NOCl (Tilden reagent) with primary amines
Why would the chloride ion attack the electron rich amine? The amine is the better nucleophile in the system, and will attack the $\ce{NO+}$. This gives a $\ce{RNH-NO}$ nitroso species which is then protonated on oxygen, loses water, and gives the diazonium cation. The resultant diazonium cation loses nitrogen rapidly and get attacked by chloride to give the primary alkyl chloride.
More can be read about this process here (which is where I sourced the reaction scheme) or by searching the term "nitrosation of primary amine"
Why would the chloride ion attack the electron rich amine? The amine is the better nucleophile in the system, and will attack the $\ce{NO+}$. This gives a $\ce{RNH-NO}$ nitroso species which is then protonated on oxygen, loses water, and gives the diazonium cation. The resultant diazonium cation loses nitrogen rapidly and get attacked by chloride to give the primary alkyl chloride.
More can be read about this process here (which is where I sourced the reaction scheme) or by searching the term "nitrosation of primary amine"
Why would the chloride ion attack the electron rich amine? The amine is the better nucleophile in the system, and will attack the $\ce{NO+}$. This gives a $\ce{RNH-NO}$ nitroso species which is then protonated on oxygen, loses water, and gives the diazonium cation. The resultant diazonium cation loses nitrogen rapidly and get attacked by chloride to give the primary alkyl chloride.
More can be read about this process here (which is where I sourced the reaction scheme) or by searching the term "nitrosation of primary amine"
Why would the chloride ion attack the electron rich amine? The amine is the better nucleophile in the system, and will attack the $\ce{NO+}$. This gives a $\ce{RNH-NO}$ nitroso species which is then protonated on oxygen, loses water, and gives the diazonium cation. The resultant diazonium cation loses nitrogen rapidly and get attacked by chloride to give the primary alkyl chloride.
More can be read about this process here (which is where I sourced the reaction scheme) or by searching the term "nitrosation of primary amine"
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