joe_aldehyde
Hazard to Self
Posts: 68
Registered: 26-3-2005
Member Is Offline
Mood: what is mood?
|
|
HBr addition to propenylbenzenes?
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
Hazard to Others
Posts: 185
Registered: 21-10-2003
Location: South Side Tejas [Cloverland]
Member Is Offline
Mood: Inside looking out
|
|
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.
\"Abiding in the midst of ignorance, thinking themselves wise and learned, fools go aimlessly hither and thither, like blind led by the blind.\" -
Katha Upanishad
|
|
|
joe_aldehyde
Hazard to Self
Posts: 68
Registered: 26-3-2005
Member Is Offline
Mood: what is mood?
|
|
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 :-/
|
|
|
![[*]](images/xpblue/default_icon.gif){kind=icon}
