Talk:Johnson–Corey–Chaykovsky reaction

Johnson–Corey–Chaykovsky reaction has been listed as one of the Natural sciences good articles under the good article criteria. If you can improve it further, please do so. If it no longer meets these criteria, you can reassess it.

Article milestones
Date	Process	Result
February 25, 2011	Good article nominee	Listed

A fact from this article appeared on Wikipedia's Main Page in the "Did you know?" column on January 18, 2011.

The text of the entry was: Did you know ... that the Johnson-Corey-Chaykovsky reaction, now used in a total synthesis of chemotherapeutic drug taxol, was developed after an attempted Wittig-like olefin synthesis yielded an epoxide instead?

TODO[edit]

THERE IS TWO DIFFERENT NAMES (JACOBSEN AND JOHNSON) FOR THIS REACTION IN THIS ARTICLE (ALSO IN THE BOX ON THE RIGHT). — Preceding unsigned comment added by 2001:4CA0:2615:1:FD6C:FF1C:6614:A9FF (talk) 07:07, 23 October 2018 (UTC)[reply]

Discuss mechanism. DMacks (talk) 06:09, 17 September 2009 (UTC)[reply]

Expansion[edit]

I've expanded the article but I'm unsure of some of my sectioning; the section titles don't exactly match the template set by the WikiProject but the line between scope and variations for this reaction is blurry so I decided to separate it into racemic/substrate-directed diastereoselective versions and enantioselective versions. Any suggestions about how to better separate it would be appreciated. Mdlevin (talk) 00:32, 3 January 2011 (UTC)[reply]

GA Review[edit]

This review is transcluded from Talk:Johnson-Corey-Chaykovsky reaction/GA1. The edit link for this section can be used to add comments to the review.

Reviewer: Nergaal (talk) 07:31, 24 February 2011 (UTC) GA review – see WP:WIAGA for criteria GA review – see WP:WIAGA for criteria[reply]

This article looks pretty good at a quick read

Is it reasonably well written?
A. Prose quality:

B. MoS compliance for lead, layout, words to watch, fiction, and lists:
I would prefer to have a short history section to which to move the second paragraph from the lead. Also, the intro should talk a bit more about the actual contents of the article like any abstract of journal article would.
Is it factually accurate and verifiable?
A. References to sources:

B. Citation of reliable sources where necessary:

C. No original research:
Is it broad in its coverage?
A. Major aspects:
Needs a history section

B. Focused:
Is it neutral?
Fair representation without bias:
Is it stable?
No edit wars, etc:
Does it contain images to illustrate the topic?
A. Images are copyright tagged, and non-free images have fair use rationales:

B. Images are provided where possible and appropriate, with suitable captions:
Overall:
Pass or Fail:
Will go through in detail with some specific concerns

It is a good chemistry article that I wish we had lots of. I am a bit worried that it is a very technical article, I believe that it should be ok for a good article. Keep in mind to wikilink all the first instances of technical terms for all those freshman chemists that might visit this page. Nergaal (talk) 07:47, 24 February 2011 (UTC)[reply]

Now specifics:

I would prefer to move the second paragraph into a separate history section; it might sound weird, but for a wikipedia article some sort of background is necessary
you use bolding too much. If you want to emphasize something, use italics.
the chemical names should not be capitalized
"The reaction mechanism for this reaction type consists" repetition

"myriad" I am not sure this is a very encyclopedic word

wikilink electorpyle

File:CCReagentGeneral.png: move this to the right side instead of centering it

sulfoxonium what? reagent?
"(no thionyl)" I don't udnestand this
"The vast majority of reagents have either R1 or R2 as hydrogen." please define R1 and R2 without the need of image
also, what is R typically?
File:AziridinationCCR.png is not an example of a synthesis of an aziridine.
there is no mention of solvent scope. is it whatever the reagents are soluble in? same for temperature. is low temperature ever necessary? should there be a separate section on preparation which would include reagents, solvents, temerature range and other conditions?
the article never defines ee used in the images. the enantioselective introductory paragraph should explain this as if the reader is not an organic chemist
File:CCRchiralcat.png does not clearly show that the molecules below the reaction are in fact the sulfide on the reaction arrow.
unlink Varinder Aggarwal
this article is heavily geared towards organic chemists. I hope the comments above will make it more accessible to readers outside of the field.
feel free to use Oligonucleotide synthesis as a model for some issues

Nergaal (talk) 08:11, 24 February 2011 (UTC)[reply]

Revisions[edit]

In response to your above comments, I've made the following revisions:

Created a history section.
Much of the bolding changed to italics
Capitalization errors fixed
Rephrased intro to reaction mechanism section
"myriad" changed to many
electrophile wikilinked
File:CCReagentGeneral.png moved to the right
Types of ylides section revised to be clearer and avoid outright references to the image
For File:AziridinationCCR.png, the first example is the synthesis of an aziridine, but I added a short sentence explaining the relevance of the second example.
wikilink to enantiomeric excess added at the beginning of the enantioselective variant section
Added the word "below" to File:CCRchiralcat.png and added a sentence above the image explaining it.
wikilink to Varinder Aggarwal removed

My only disagreement is with the idea of including temperature, solvent, or other reaction conditions. I find that sort of material to be too specific for wikipedia. Most academic papers leave that to supporting information, and it is almost never in a review unless the solvent or temperature effects are very important to the reaction. Wikipedia is certainly not where someone wishing to actually run the reaction would turn for those sorts of details. I'm of course willing to discuss this issue further.

Hope the revisions are to your liking. M.Levin 23:26, 24 February 2011 (UTC)[reply]

I'll pass the article in the current state. Considering its scope, the article in of good quality. Good job and good luck with your future contributions. Nergaal (talk) 01:10, 25 February 2011 (UTC)[reply]

"the sulfonium cation is a good leaving group" - dimethyl sulfide is a good leaving group, not the corresponding carbocation.89.69.82.3 (talk) 10:47, 5 November 2012 (UTC)[reply]