Sciencemadness Discussion Board

hbr adds to double bond

xxxxx - 28-2-2008 at 06:02

attached image describing the addition of hbr to double bond

EDIT by Nicodem: Removed the annoying neck breaking picture (Solo reposted it rotated).

[Edited on 28/2/2008 by Nicodem]

LSD25 - 28-2-2008 at 06:18

OK, I now have a cricked neck - what do you want to say? Having taken note of your apparent unwillingness to state your object in having posted such picture, I'll have to make some assumptions - if this offends, so be it.

How do you intend to get to anything useful (I'll take a stab in the dark here) unless of course you then demethylate the a-bromoeugenol and methylate it at the 3,4 position prior to aminating the bromohydrin?

Does the HBr still add to the double-bond of the 3,4-dihydroxy variant?

If so, wouldn't it be better (or at least more practical) to demethylate first (presuming this is what you want to do)?

If not, is it possible to form a bromohydrin from the demethylated product?

Do you think that the methylenation of the dihydroxy variant would affect the bromohydrin?

Further to which, assuming you intend to methylate the phenolic hydroxyl's (another assumption, I know) - does the methylated product form a bromohydrin? Is it what you wanted?

Lastly, should you perhaps methylate the hydroxyl's before aminating? If not, how do you intend to prevent the formation of secondary (assuming that is not what you want), tertiary & quaternary amines?

PS is it possible to rotate that picture so that it can be read without turning ones head on its side?

Oh, yeah, although they say that a picture is worth a thousand words, it would probably be better if you took the time to explain the purpose of the picture?

[Edited on 28-2-2008 by LSD25]

PS I'm not meaning to be a prick, but what do you expect? I've had my arse tanned (figuratively) for making more of an effort than that....

[Edited on 28-2-2008 by LSD25]

solo - 28-2-2008 at 07:27

This might help....also can you post the name of the textbook /journal from where you took the information from......thanks......solo









[Edited on 28-2-2008 by solo]

Reference Information

solo - 28-2-2008 at 11:42

The Synthesis of 3-Methylisopuinolines. Part I.
G. R. CLEMO and J. H. TURNBULL.
J .Chemical Society pp. 533, 1945

Attachment: The Synthesis of 3-Methylisoquinolines. Part I ..pdf (326kB)
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