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Author: Subject: Oxalyl Chloride Challenge
Texium (zts16)
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[*] posted on 15-12-2018 at 11:55


Quote: Originally posted by JJay  
I will be actively working to synthesize oxalyl chloride next week. I'll check back, and if someone has actually beaten me to the punch then I'll award the prize, but I have an advantage: under the rules, as the contest sponsor, I am permitted to use phosphorus compounds. So if you have a winning entry, now is the time to submit it.
Yeah, I don't see anything about that in the OP. Lame.
But if you want to race, I could probably whip up some PCl5 next week...




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JJay
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[*] posted on 15-12-2018 at 13:47


Quote: Originally posted by Texium (zts16)  
Quote: Originally posted by JJay  
I will be actively working to synthesize oxalyl chloride next week. I'll check back, and if someone has actually beaten me to the punch then I'll award the prize, but I have an advantage: under the rules, as the contest sponsor, I am permitted to use phosphorus compounds. So if you have a winning entry, now is the time to submit it.
Yeah, I don't see anything about that in the OP. Lame.
But if you want to race, I could probably whip up some PCl5 next week...


Read the fine print.

I have a few things on my plate. You can probably do it faster, but the prize is for a non-phosphorus synth. Or if you want, you can take charge of the challenge, but then you have to award the prize. Up to you. I keep my word.




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clearly_not_atara
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[*] posted on 15-12-2018 at 14:20


Ok, I have one more stupid idea.

Suppose your starting materials are ethyl bromide, thiocyanate, DMSO, and acetyl chloride.
The first two give ethyl thiocyanate.
The second two give chloromethyl methyl sulfide:
https://pubs.acs.org/doi/abs/10.1021/ja01608a016?journalCode...

It should be possible to perform a Barbier-like reaction between these two to get ethyl thiomethylthioacetate. Chloromethyl methyl sulfide is likely to be a noxious chemical, but it should be less volatile than Me2S.

Oxidation with SeO2 should give oxalyl methyl-ethyl dithioester, which then might interact with SO2Cl2 to give oxalyl chloride.



[Edited on 15-12-2018 by clearly_not_atara]




[Edited on 04-20-1969 by clearly_not_atara]
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Texium (zts16)
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[*] posted on 15-12-2018 at 18:25


Quote: Originally posted by JJay  
Quote: Originally posted by Texium (zts16)  
Quote: Originally posted by JJay  
I will be actively working to synthesize oxalyl chloride next week. I'll check back, and if someone has actually beaten me to the punch then I'll award the prize, but I have an advantage: under the rules, as the contest sponsor, I am permitted to use phosphorus compounds. So if you have a winning entry, now is the time to submit it.
Yeah, I don't see anything about that in the OP. Lame.
But if you want to race, I could probably whip up some PCl5 next week...


Read the fine print.

I have a few things on my plate. You can probably do it faster, but the prize is for a non-phosphorus synth. Or if you want, you can take charge of the challenge, but then you have to award the prize. Up to you. I keep my word.
I see no fine print to read.

I even searched for "phosphorus" on the first page of this thread and it was only mentioned twice- once in the OP where you said "You must synthesize oxalyl chloride without using any phosphorus compounds" and a second time in the quoted post.




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JJay
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[*] posted on 15-12-2018 at 18:43


Quote: Originally posted by JJay  

5. I reserve the right to close the competition before any submissions are received by producing oxalyl chloride in my own lab.







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[*] posted on 15-12-2018 at 18:48


Don't know what has you so upset Jjay. This seems like an overreaction.
I hope you reconsider. You will be missed.
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[*] posted on 15-12-2018 at 22:12


I'd tried to reply to this thread earlier but it was closed, j_sum1 suggested I post it here.

I thoroughly enjoy your contributions JJay, and style of writing/debate e.g. [1][2].

Reminds me of reading through early 1900s scientific proceedings, authors have interesting argumentation and style (in this page, lavish praise for Dr. Cook) (somewhere in a different volume/book an author when challenged said if he was shown wrong, to treat his writing as detritus, reminded me of this forum).

To illuminate an example of what I believe JJay was referring to as blatant self-promotion, see my posting here and later that page Melgar here. I chuckled extensively but my intention was never to maintain such a script, but after writing it to try to pawn it off on someone else to maintain and run, such as streety. I really am a "lazy" programmer, I hate to do tasks outside of what I'm principally focused on and I pawn such tasks/projects off for others to do at work. I hardly have the focus/energy to do everything I do want to do.

My motivation in things is to learn, share knowledge, and teach; I don't care for praise or recognition. It brings me joy to bring others success! On this topic I am thankful for the efforts Melgar and streety had made (and countless others for their efforts on different subjects). Though I guess there are other things which bothered JJay in this matter, e.g. the suggestion of compensation for tasks, running contrary to the spirit of this forum (I'm sure this could be articulated better, but I have shopping to do before this night is through!).

[Edited on 16-12-2018 by andy1988]
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