Talk:Sigmatropic reaction

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Do the bottom two pictures for hydride and methyl shifts conserve carbon atoms? It looks like notation is changed from the left side of the reaction to the right side: from a line representing a carbon-carbon bond to a line indicating both CC and CH bonds.

I would edit it, but I'm not an o-chemist. I agree, you've lost a methylene in both cases - sort it out!

• Thanks for pointing out the mistake, correction made V8rik 19:07, 28 March 2007 (UTC)

Also want to add that SIGMATROPIC is the name of one of the most important bands to come out of the Greek scene. They have worked with sich greats as Cat Power and Carla Torgenson of THE WALKABOUTS. The Alternative Electronica group headed up by AKIS BOYATZIS of CAPTAIN NEFOS fame disbanded in 2008 when 2 members moved to California to form a new outfit called WE GOVERN WE. —Preceding unsigned comment added by 97.94.112.101 (talk) 21:47, 13 March 2009 (UTC)

this revised article seems to be of decent quality, it should be rated, and critiqued so as to provide direction for further improvement. —Preceding unsigned comment added by 140.233.209.43 (talk) 00:03, 19 June 2009 (UTC)

Revised article is of superior quality to previous article. —Preceding unsigned comment added by 24.61.254.56 (talk) 06:25, 14 July 2009 (UTC)

Most of the "original" material added back in by V8rik seems superfluous and disjointed with the rest of the revised article. Besides the information about lewis acid catalysis, isn't the rest of the information better explained in the article as a whole? —Preceding unsigned comment added by 140.233.209.67 (talk) 00:10, 15 July 2009 (UTC)

The material added back in by V8rik now seems to be better synthesized with the rest of the article. —Preceding unsigned comment added by 140.233.209.67 (talk) 00:15, 15 July 2009 (UTC)

recommendation for the following:

Comments

To be a real A-Class a short history section and a section on applications would be very nice. The history section should mention the first observed Sigmatropic reaction and who observed it, also important would be a ref to the publication in which the word sigmatropic was first used. A applications section should mention a important use of the reaction in industry to show why it is of interest for other people than chemists. Neither of the two section should be a full coverage of all the mentioned subreactions and all their discoverers and all their applications.--Stone (talk) 09:26, 14 November 2009 (UTC)

And by applications, not another total synthesis paper. Applications = making compounds that are sold for a profit...It is nice to touch on the real world where nonacademic readers could see a connection.--Smokefoot (talk) 15:58, 14 November 2009 (UTC)

Absolutly! Stuff which everybody has at home would be best, applications in science do matter for scientist, but they are very boring for everyday people,--Stone (talk) 18:28, 14 November 2009 (UTC)

I absolutely (Note the spelling) disagree. The sigmatropic (Note, no upper case S in English) reaction is an important (note the use of the indefinite article "an" before words beginning with a vowel and some words with the letter h) class of pericyclic reactions. One needs only to follow the links back to "pericyclic" or "Woodward-Hoffmann rules" to get the history and applications. These reactions are taught in first-year Organic Chemistry and are important to anyone taking chemistry at that level. Organic Chemistry at home? Really, now. Boring for everyday people? So is second order electric susceptibility but you need to know it for understanding nonlinear optics (and you can get a detailed explanation of NLO in Wikipedia.) Making compounds that are sold for a profit? Nonacademic readers could see a connection? I think you are missing the whole point of Wikipedia and certainly Organic Chemistry. By the way, I give to grammar the same high regard as I do to logic, of which grammar is an application.Laburke (talk) 05:30, 20 June 2010 (UTC)

Why do you write organic chemistry as Organic Chemistry, then? :P

Have a look at our articles Linguistic prescription#Prescription and description in conflict and Hypercorrection.

Ben (talk) 08:01, 20 June 2010 (UTC)

• A lot of material is redundant: articles exist already for example Cope rearrangement. Suggest trimming down the article and move content to specialist pages V8rik (talk) 17:18, 14 November 2009 (UTC)

Lumisterol conversion to vitamin D

conversion of lumisterol to vitamin D

The reaction pictured doesn't look right. The alterations to the side chain (loss of a methyl group and a double bond) do not appear to be explained by the mechanism which is drawn. Is the final product drawn correctly? --Robert.Allen (talk) 06:38, 1 August 2010 (UTC)

I found the this reference which supports the notion that the product of this reaction is vitamin D2 not vitamin D3. However, it does not provide the proposed mechanism of a 1,7-shift, so we still need to find a reference for that. However, I think it is enough to go ahead and change the product of the pictured reaction to D2:

conversion of lumisterol to vitamin D

--Robert.Allen (talk) 16:58, 1 August 2010 (UTC)

• Thanks for spotting the error, vitamin D2 is confirmed in Carey&Sundberg V8rik (talk) 21:10, 1 August 2010 (UTC)

Woodward-Hoffman Sigmatropic Shift Nomenclature

Maybe I am just missing something here (I'm tired), but is the 1,5 product in the diagram actually the 1,3 product? They look the same. Shouldn't the H be on the 5th C? Marcipangris (talk) 21:59, 8 August 2010 (UTC)

Should now be OK. --Robert.Allen (talk) 04:52, 21 September 2010 (UTC)