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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: magos on March 05, 2015, 08:58:20 AM

Title: Help in synthesis of this molecule
Post by: magos on March 05, 2015, 08:58:20 AM

I have this molecule and I have no idea how to even start synthesis. Please help

Attachment within.

Thank you
Kyriakos

Title: Re: Help in synthesis of this molecule
Post by: Arkcon on March 05, 2015, 09:11:08 AM

Welcome, magos: to the Chemical Forums.  Please trouble yourself to read the Forum Rules{click} (http://www.chemicalforums.com/index.php?topic=65859.0), we want to see your attempt.

Its generally rare for a beginning Organic chemistry student to be given a complex molecule with no hint as to where to start.  Can you at least give us some starting materials?

Title: Re: Help in synthesis of this molecule
Post by: magos on March 13, 2015, 05:27:15 AM

I found out how to get to this point
and i want to get one step further
is there any way to do this without using hazardous cyanating reagents?

Title: Re: Help in synthesis of this molecule
Post by: tomek on March 13, 2015, 05:58:24 AM

I would recommend consulting this paper:
http://pubs.acs.org/doi/abs/10.1021/jo00077a017

Title: Re: Help in synthesis of this molecule
Post by: kriggy on March 13, 2015, 06:42:11 AM

THe good point is to identify the functional groups and then think how than can be made. For example, the cyano group can be added using CN^-, but there are another ways like dehydratation of amide etc..

Title: Re: Help in synthesis of this molecule
Post by: magos on March 13, 2015, 07:00:15 AM

thank u very much tomek and kriggy
tomek can you recommend me a site which can open that article?

Title: Re: Help in synthesis of this molecule
Post by: Dan on March 13, 2015, 07:18:05 AM

Quote from: magos on March 13, 2015, 07:00:15 AM

tomek can you recommend me a site which can open that journal?

Your University should have a subscription. Usually you have to view the journal from a university IP address (either by being connected to the university network or using VPN) or go through some sort of login procedure, which can vary depending on how your university's access is set up.

If you don't know how to do it, you will have to ask library services at your university or pay for the article (it is against the Forum Rules to request an illegal copy).

Title: Re: Help in synthesis of this molecule
Post by: magos on March 13, 2015, 07:38:50 AM

ok Dan i will ask library services at my university, i understand and respect the forum rules

Title: Re: Help in synthesis of this molecule
Post by: magos on April 01, 2015, 02:37:05 AM

Can anybody help me with that mechanism? i think that is  correct but i want a second opinion!
it is my first stage for my synthesis

Title: Re: Help in synthesis of this molecule
Post by: Dan on April 01, 2015, 02:47:57 AM

The first step is incorrect. With the arrows as you have drawn them, which group on C is leaving?

Title: Re: Help in synthesis of this molecule
Post by: magos on April 01, 2015, 03:52:25 AM

 :( o ??? k how about that?

Title: Re: Help in synthesis of this molecule
Post by: Dan on April 01, 2015, 05:17:53 AM

What are the reaction conditions? We need to know if the conditions are acidic or basic to write a reasonable mechanism. Also what is the ratio of the reactants? Hint: I think more than 1 equivalent of S₂Cl₂ is required.

The direction of electron flow in your first step is ok - i.e. the arrows are all going in the right direction - but your use of curly arrows is a bit strange/unconventional.

Some of the arrows in the second step are the wrong way round. You need to keep track of charge, which way are the electrons flowing? Remember that electrons flow to the arrowhead, and will leave a negative charge there. A positive charge will be left at the tail of the arrow.

The third step is incomplete (what happent to the S-Cl bond?)

4th step in your originally proposed mechanism is wrong (charge balance).

Title: Re: Help in synthesis of this molecule
Post by: magos on April 01, 2015, 05:53:26 AM

i have 0.265 mol ClCH2CN and 0,62mal S2Cl2 and 50 ml CH2Cl2