joe_aldehyde - 1-4-2005 at 03:02
if for example isoeugenol, which is 1(3-methoxy-4-hydroxyphenyl)prop-1-ene, is refluxed with HBr to effect demethylation and hydrobromination to the
double bond, which product is being favored, the 1-bromo- or 2-bromo-compound? or are both products equally formed? will the steric hindrance
introduced by the phenyl substituent have any effect on the course of the reaction?
[Edited on 1-4-2005 by joe_aldehyde]
chochu3 - 2-4-2005 at 02:03
The bromine will add to the benzylic carbon because of resonance causing more stability. This is true with all addition reactions of styrene type of
compounds. Nucleophile will add to benzylic carbon.
joe_aldehyde - 2-4-2005 at 03:44
well, then the oxidative photoamination of y-methylstyrenes is the only way to go. i have yet to build an apparatus in which this rxn could be
accomplished.
quite hard to control a 500W super pressure mercury lamp :-/