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Topic: Intramolecular Friedel-Crafts' cyclization mechanism  (Read 2939 times)

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Offline Rutherford

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Intramolecular Friedel-Crafts' cyclization mechanism
« on: October 27, 2012, 05:22:33 AM »
I need to write the mechanism for a intramolecular Friedel-Crafts' cyclization (I am not sure about the name). My attemp is attached so I need someone to check it (C6H5CH2CH2COCl is the reactant) :
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Offline discodermolide

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Re: Intramolecular Friedel-Crafts' cyclization mechanism
« Reply #1 on: October 27, 2012, 05:30:18 AM »
I don't like the acylium cation but this says otherwise:
http://en.wikipedia.org/wiki/Friedel–Crafts_reaction

I suppose it is stabilised by involving the lone pair of the oxygen to give the C triple bond O+.
Otherwise the mechanism looks OK.
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Offline Rutherford

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Re: Intramolecular Friedel-Crafts' cyclization mechanism
« Reply #2 on: October 27, 2012, 06:47:32 AM »
I remember that I read on chemguide that it is -C+=O, but it is probably simplified there, so I thank you for your correction.
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