Notice the change in the position of the double bonds.
I have a confusion. According to me it should depend on the structure given.
P.S. How do I insert a subscript/superscript ?Nicodem - 11-12-2010 at 12:36
Check DOI:10.1016/S0040-4020(02)01563-6. There should be something on regioselectivity of benzyne formation and nucleophilic addition, but I don't have
the time to read that.Claisen - 11-12-2010 at 12:45
That is a paid site.
I have a book which explains the regioselectivity but it does not say anything about major/minor product.DDTea - 11-12-2010 at 21:52
Looking at this, I'm really tempted to say that m-methoxyanisole ought to be the major product because a) it forms from both pathways and b)
it is the major product in one of those pathways. Of course, this assumes a 50/50 split at the beginning regarding the location of the benzyne triple
bond. TheOrbit - 11-12-2010 at 21:54
-OCH3 by mesomeric effect place -ve charge on O- & P- so it hinder the attack of the -ve NH2 on this position make m- more stable
Orbit, that drawing and explanation are great, but it's m-bromoanisole undergoing this reaction. Only the ortho and para position are adjacent to the
bromide-subsituted carbon. Which proton would be preferentially attacked by -NH2?TheOrbit - 12-12-2010 at 03:46
DDTea , we apply the same principle of O- , P- -ve charge . so m- NH2 will be preferable Claisen - 12-12-2010 at 06:33
I too think that meta product will be major.
Actually my book says that ortho is the major & para is minor but now I believe that its wrong.spirocycle - 12-12-2010 at 06:56
^call the publishing company and you can get some cashClaisen - 14-12-2010 at 08:14
That is a paid site.
I have a book which explains the regioselectivity but it does not say anything about major/minor product.
Scientific books have references, so check the reference!
I also gave you a reference for a review paper, yet you did not even bother checking it. I find your "That is a paid site" excuse offensive, because
we are all in the same boat and someone has to get it in some way or the other, either via proxy servers, VPN's or by going to the library. Find it here.
