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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: insertwittyname on March 25, 2014, 12:44:42 PM

Title: Hoffman eleimination cyclic amine
Post by: insertwittyname on March 25, 2014, 12:44:42 PM

How does one get a Hoffman elimination in a cyclic amine?
I manage acyclics fine, but if it is a cyclic amine, one of the carbons doesn't have a full valency (pls see attached file for a clearer idea).
Does anybody have any idea how to do this?

Title: Re: Hoffman eleimination cyclic amine
Post by: AlphaScent on March 25, 2014, 02:33:31 PM

It needs to be a quternary ammonium salt.  You have it written as a tertiary amine.  Which is stable. 

This is not going to proceed in a typical Hofmann elimination giving a "Hofmann" olefin.