[missUK11]

I am really struggling with this reaction mechanism below, please can someone give me some tips, i would really appreciate it

i have identified in the product a cyclic 1,4-diketone....not sure if that helps much though

Many thanks in advance.

[orgopete]

What would happen if you protonate the nitrogen?

[missUK11]

What would happen if you protonate the nitrogen?

it would form a nitrillium ion...then would i be able to hydrolysis it to a carboxylic acid ? if so what could i do next :/

[Guitarmaniac86]

What would happen if you protonate the nitrogen?

it would form a nitrillium ion...then would i be able to hydrolysis it to a carboxylic acid ? if so what could i do next :/

What could you convert the carboxylic acid to that would enable you use AlCl₃?

[missUK11]

What would happen if you protonate the nitrogen?

it would form a nitrillium ion...then would i be able to hydrolysis it to a carboxylic acid ? if so what could i do next :/

What could you convert the carboxylic acid to that would enable you use AlCl₃?

An acid chloride but i am not given Alcl3 in the reaction

[orgopete]

it would form a nitrillium ion...then would i be able to hydrolysis it to a carboxylic acid ? if so what could i do next :/

Do you think a nitrilium ion might be an aza equivalent to an acylium ion?

[MariaJohn]

You can try this link:
http://www.sciencedirect.com/science/article/pii/S1044030598000683

[orgopete]

My point was that if an acylium ion can undergo an electrophilic attack, then a nitrilium ion might react in the same way. Had the poster tried that analogy, they would have been one step from their product.