I have the papers on clarke eschewieler cyclicicyzations and other pertinent reactions simliar to this so you can understand the mechamisms.
let me know, I thought I already sent this to you.
in the case of say for example, alpha-methyl-styrene, reaction with, trimethyl,triazine, aka. trimethyl trimethylene,triamine, and propionic acid.
the mechanism is a an aminomethylation of the alkene followed by formation of the tertiary carbonioum ion (the pre cyclization intermediate) which is then saturated by the carboxylic acid, this explains why this procedure works like a dream, and without any hitches the mechanism is beautiful..
Email me you know who I i am.
and to clarify, I have studied the mechanism in concert with others well educated in chemistry and we can conclude that methyl phenyl tetrahydropyridine is not a by-product of this reation by mechanistic studies.
Believe me I would not lie about this.
the key is to exclude water completely!!! Since tertiary alcohols are the easieast to dehydrate and in this reaction scheme water is needed to cause this hydrolysis, it is imperative to exclude water.
Hence the use of amino methylation reageants as trimethyl triazine as oppopsed to it's cousin, the amino formaldimine
in the prescence of H2O?
BTW those heavier amines give way lower yields due to thier solubilty in the reation matrix.
I.E. phenyl-ethylamine.
for example.