xxxxx - 28-2-2008 at 05:50
i am attaching a paper which describes the addition of nitrogen to a double bond. i was wondering if this might be applicable to substituted allyl or
propenyl benzenes.
EDIT by Nicodem: This is the fourth time you post an unrotated scan without a reference and without explaining what is the point of your post!
If this is some kind of trolling it trully is of an annoying kind. You better do not do it again.
Removed the annoying neck breaking picture (Solo reposted it rotated).
[Edited on 28/2/2008 by Nicodem]
solo - 28-2-2008 at 07:40
Again what book are you taking apart as the reference......i would like to know .......solo
PHILOU Zrealone - 28-2-2008 at 07:45
Seems to be a beautiful Michaël addition-elimination 
R-CH=CR'-CR"=O <--> R-CH(+)-CR'=CR"-O(-)
Via (-CO)2-N-Na
I would have thought the methacrolein or the phtalimide to be unstable in basic media but is is apparently not the case
Reaction must work for the molecule you proposed.
Reference Information
solo - 28-2-2008 at 08:05
1,4 Addition Reactions. III. The Addition of Cyclic Imides to --Unsaturated Aldehydes. A Synthesis of -Alanine Hydrochloride
Owen A. Moe, Donald T. Warner
J. Am. Chem. Soc. 1949; 71(4); 1251-1253.
Excerpt
........If 1,2 addition had occurred, the presence of
unsaturation in the reaction product could be
readily determined by low pressure hydrogenation
employing palladium on charcoal as the catalyst.
In an experiment designed to determine this
possibility (using methacrolein-succinimide reaction
product) it was found that less than 5%
of the theoretical amount of hydrogen had been
consumed after one hour. However, when acetic
acid, ethyl cyanoacetate and piperidines were
added to the same reaction mixture, and hydrogenation
was resumed, 67% of the theoretical
amount of hydrogen was taken up in one hour,
indicating the predominant presence of the
aldehydo compound.
Attachment: 1,4 Addition Reactions. 111. The Addition of Cyclic Imides to a,p-Unsaturated Aldehydes. A Synthesis of p-Alanine Hydroc (381kB)
This file has been downloaded 538 times
not_important - 28-2-2008 at 08:26
Yeah, Philou has it, and I agree with Solo - hard to read rotated scans from an unstated book is a little impolite. Scan it in high enough
resolution, crop it down to the portion of interest and only upload that part. If you don't have software that can do that, pick up the Gimp or
impshop, or if you are running Windows get IrfanView - all of those are free.
Try these relate
Solvent-free, catalyst-free Michael-type addition of amines to electron-deficient alkenes
http://www.arkat-usa.org/ARKIVOC/JOURNAL_CONTENT/manuscripts...
Michael Additiion of Alkyl Amine to α,β-Unsaturated Carbonyl Compounds Catalyzed by KF/Al2O3
http://www.imm.ac.cn/journal/ccl/1508/150801-883-03-0526-p2....
Cerium(IV) ammonium nitrate (CAN) catalyzed aza-Michael addition of amines to α,β-unsaturated electrophiles
doi:10.1016/j.tetlet.2006.05.182
http://www.sciencedirect.com/science?_ob=ArticleURL&_udi...
LiClO4 Accelerated Michael addition of amines to α,β-unsaturated olefins under solvent-free conditions
http://www.organic-chemistry.org/abstracts/literature/703.sh...
and a whole slew listed in Organic Reactions in Water: Principles, Strategies and Applications
http://books.google.com/books?id=f_VvZgKumagC&pg=PT269&a...
But those mostly require electron-withdrawing groups attached to the alkene functionality. What you want to look at is reactions similar to this
attachment,
Attachment: tan.pdf (65kB)
This file has been downloaded 751 times
chemrox - 28-2-2008 at 19:35
As for the topic its hardly new and the last time he did this he wouldn't repost the upright pages are ref the doc. This kind of thing is the most
irritating of all. I'd almost prefer, "How is ozone made?" That said, @not_important treats us to some nice articles-thank you very much. The
software references were a nice touch too. Best of all this last-tan.pdf. Saved the f88king post.