The reaction between a dihalomethane and a hydroxyl/alcohol group
It is known that catechols or other molecules with two hydroxyl groups in the ortho position on a benzene ring can be deprotanated by a base after
which a dihalomethane can react and close the ring. This forms a methylenedioxy group. I also understand that there is a risk of dimer formation if
two dihalomethanes connect two of the substrate molecule together.
If a molecule was to be methylenated like this, and there was a hydroxyl group also at the other end of the molecule, brancing from a chain on the
other side of the benezene ring, but by itself, would the dihalomethane irreversibly bind to this, leaving the other half of the dihalomethane
dangling, or even worse, to chain-connect with the end of another molecule?
I understand that once the methylenedioxy ring is formed, it doesn't easily get deprotanted in the solution. I am not clear about the other aspects.
Will a dihalomethane recklessly bind to any deprotanted hydroxyl group in such a reaction?
For instance:
Is this bond able to be formed from R-OH:
R-O-CH2-Br as a side reaction?
If so, can that be cleaved to remove the CH2-Br, or even possibly hydrogenating it to a R-H type situation, seding a CH3-Br into the solution?
Edit:
Answered my own question with some additional research. Feel free to delete this. Apperently a -COOH group would not be effected in a substituion
reaction even if deprotanated because the oxygen double bond and oh bond form a sort of resonance stability that is far less reactive than a lone -OH
group
[Edited on 24-1-2014 by Electra]
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