[lutesium]

Dear Sir/Ma'am

I have a paper showing that =S can be replenished by a piperidine group this may mean that amination can be done directly by the =S group!!! but how can we add that =S group to the Carbon skeleton??? Can you tell me a name reaction for it???

Wilsmeier Haack reaction: Can someone explain it? NNDimethylformanilide + POCl3 's role in it???

Bz-C=O-NH + POCl3 + R-NH2 ===> Bz-C-(NH-R)=NH
What is this Reaction??? If you can give me a name reaction covering this reaction I'd be grateful!!!


Lutesium...

[macman104]

I have a paper showing that =S can be replenished by a piperidine group this may mean that amination can be done directly by the =S group!!! but how can we add that =S group to the Carbon skeleton??? Can you tell me a name reaction for it???

Can you provide a citation for the paper?

Wilsmeier Haack reaction: Can someone explain it? NNDimethylformanilide + POCl3 's role in it???

There is a very good mechanism on the wikipedia article.  The role is very clear in it.

http://en.wikipedia.org/wiki/Vilsmeier-Haack_reaction

[lutesium]

Journal of Pharmaceutical Sciences June 1964 volume 53, number 6


Lutesium...

[macman104]

Author?  Starting page?

[lutesium]

Scott J. Childress and M. I. Gluckman

Page 577 but the Reaction that I have mentioned is at the page 580

[lutesium]

hey Mac even if you find the article how will you read it??? Will you purchase it by paying ~30$ or is there another way that I don't know???


Lutesium...

[Arkcon]

If I couldn't find the paper in question in the local university library, I'd definitely search for the authors, they may have published something similar in other journals.

[macman104]

hey Mac even if you find the article how will you read it??? Will you purchase it by paying ~30$ or is there another way that I don't know???

Well, if it weren't available through my school, I'd do as Arkcon mentioned, or do an interlibrary loan and I could probably get a digital copy within a few days.

[lutesium]

Any more ideas???


Lutesium...

[macman104]

Any more ideas???

Lutesium, unfortunately, I do not have access to the article, so I am not able to help anymore with regards to that reaction.

For your reaction:

Bz-C=O-NH + POCl3 + R-NH2 ===> Bz-C-(NH-R)=NH

Is it supposed to be:

Bz-C=O-NH2 + POCl3 + R-NH2 ===> Bz-C-(NH-R)=NH

Regardless, I am not really sure about a mechanism for that reaction.  It seems to be similar to Vilsmeier-Haack though, NH pushes electrons to the carbonyl, POCl₃ get's attacked by the oxygen.  Then the amine comes in and attacks the carbon and kicks out the PO₂Cl₂.  That's my best guess. *shrug*

[lutesium]

Mods if its allowed can I upload files in here??? Because I have the article in PDF format!!! And this reaction is pretty interesting because it enables the chemist to add an amine group directly into the S= attached Carbon skeleton!!!

And for the other reaction that I've mentioned its NH because its a diazepine ring and the NH is followed by an other carbon.

By the way thanks for your concern to my posts macman!!!

[macman104]

Mods if its allowed can I upload files in here??? Because I have the article in PDF format!!! And this reaction is pretty interesting because it enables the chemist to add an amine group directly into the S= attached Carbon skeleton!!!

You cannot upload files that you would normally need to pay for.  Since the file requires either pay or a subscription, I do not believe it would be allowed to openly upload.

[lutesium]

That's why I'm asking!!! I don't want to break the rules


Lutesium...

[AWK]

I have a paper showing that =S can be replenished by a piperidine group this may mean that amination can be done directly by the =S group!!! but how can we add that =S group to the Carbon skeleton??? Can you tell me a name reaction for it???

RCOR1 + P4S10 = RCSR1
P4S10 (P2S5) exchange carbonyls in ketones, amides for C=S)

[lutesium]

So AWK you're telling me how to add the =S to the Carbon Skeleton... Is there a name reaction for it???

And I've Private Mailed you something AWK!!! Can you take it into consideration please???


Lutesium...