Talk:Organolithium reagent

possible error

It's mentioned that organolithium reagents are incompatible with O but there are several organolithium reagents listed below with O. If I new more about organolithium reagents I'd fix the issues.... —Preceding unsigned comment added by 129.22.126.43 (talk) 09:28, 24 October 2007 (UTC)

Lithium reagents are sensitive to molecular oxygen (O₂), active hydrogen functions (ROH, RNH₂, etc), and carbonyl groups (like those of ketones, aldehydes, etc) not to ether oxygens - these are usually OK in both the lithium reagent itself and the solvents used for their preparation and reactions. ChemistHans 22:35, 3 November 2007 (UTC)

Structure

I noticed the addition of the structure section by V8rik (I believe). I have some suggestions about this section. It describes some of my own research, so I will leave it to others to act on this.
1. First, there is an error in the drawing having to do with the definition of R - in the aggregate structures R = Butyl, but in the RCH2-H products, R would have to be Propyl.
2. There is a small factual error - n-BuLi in THF is actually a nearly 1:1 mixture of dimer and tetramer (at ca 0.1 M concentration) - see ref 1.
3. I would suggest that the graphic and the description of BuLi reactivity would probably be better located in the n-Butyllithium article, since the details are specifically about that reagent. A more extended structure section for a topic like Organolithium Reagents which covers a family of different compounds (numbering in the hundreds, and possibly thousands!) could include a little more coverage of the various types (monomers, dimers, trimers, tetramers, hexamers, etc), with examples of each and some discussion of what controls the aggregation states. ChemistHans 16:00, 20 August 2007 (UTC)

Grammatical correction needed

I can't correct this as I don't understand the subject matter but a correction is needed to make this sentence make sense: "The only prerequisite is the halide compound is substantially more electronegative than butyllithium." --A R King (talk) 08:18, 26 December 2007 (UTC)

• added that to the sentence to make it at least grammatically correct although chemically it still needs improvement V8rik (talk) 17:03, 26 December 2007 (UTC)
• Rewrote paragraph to clean this up. I think there is also a problem with the tetravinyltin example in the next paragraph. I believe this one works well not because the vinyl is more electronegative than the phenyl (I don't believe it is) but because the very insoluble tetraphenyltin product crystallizes out and "drives" the equilibrium.ChemistHans (talk) 20:55, 23 February 2008 (UTC)

Major update

• The sandbox article is not an expansion of the article but a complete replacement with total disregard of the existing page and with total disregard of the many contributors to this page to this date. Thanks guys, but your efforts have been futile. The new content is much appreciated but at the same time existing content vanishes. My advice: start from the existing article and then expand with new content Deleting or replacing segments is perfectly okay but only with a relevant edit summary so that people can keep track of changes V8rik (talk) 18:28, 2 December 2013 (UTC)

Chirality

So here's a question. Does lithium-halogen exchange proceed with retention or inversion of stereochemistry? Project Osprey (talk) 09:45, 6 January 2014 (UTC)

Requested move 10 September 2025

Organolithium reagent → Organolithium chemistryOrganolithium chemistry – This appears to be the only article inconsistent with the common naming pattern for organometallic chemistry articles, cf. {{ChemicalBondsToCarbon}}. 1234qwer1234qwer4 01:15, 10 September 2025 (UTC) — Relisting. Jeffrey34555 (talk) 05:24, 17 September 2025 (UTC) — Relisting.  veko. (user | talk | contribs) he/him 18:15, 25 September 2025 (UTC)

• Support, at least preliminarily because maybe someone will have good reasons not to do so. Organolithium chemistry title would be parallel with other Organoelement articles. The implication of retitling as organolithium chemistry would be to transfer some of the organic synthesis oriented content to more specialized articles.--Smokefoot (talk) 01:56, 10 September 2025 (UTC)
• Support move per nom and Smokefoot, consistency with related article titles. I'm not so sure the specialized "reagent" content needs to be removed because of the proposed title change, as it is certainly part of "organolithium chemistry"; however, it appears this is inappropriate regardless and at this time I would defer to other editors on these content decisions. --MYCETEAE 🍄‍🟫—talk 21:47, 11 September 2025 (UTC)

Weak oppose per Mdewman6 and explicit allowances at Wikipedia:Naming conventions (chemistry)#Organometallic compounds. I'm essentially neutral on the question but since WP:TITLECHANGES require a good reason to move a page and the current title isn't "broken", this tips the scales in favor of maintaining the current title. As a general matter, I think an "Organoelement chemistry" article that mostly covers the compounds' use as reagents would be fine but if a change is not an improvement we should let it be. --MYCETEAE 🍄‍🟫—talk 15:25, 16 September 2025 (UTC)

• Oppose until/unless there is a major restructuring of the article content. Currently, the article focuses on organolithium reagents, so the best title is its current one. Indeed, when faced with this issue when updating the chemistry naming conventions, this case was specifically mentioned (disclosure, by me) Some flexibility can be used if the article is heavily weighted toward a specific topic, such as the case for organolithium reagent, so long as the other forms redirect there. Mdewman6 (talk) 20:28, 12 September 2025 (UTC)

The opposition to the move disappoints me, but upon reflection only because I like the series of articles Organoelement compounds. Now, I am trying to figure out if there is a difference between the reagents and the chemistry. For example, maybe the OrganoLi compounds would summarize a lot of structural chemistry.--Smokefoot (talk) 16:28, 16 September 2025 (UTC)

I am trying to figure out if there is a difference between the reagents and the chemistry. I'm puzzling over this, too. There is a lengthy structure section in the article. Is content omitted or de-emphasized here that might be featured (more) prominently in an "Organolithium chemistry" article? I'm also thinking about the application of WP:DUE. If reagent chemistry is a significant part of the notability, it makes sense for the "chemistry" article to devote substantial coverage to this. --MYCETEAE 🍄‍🟫—talk 18:47, 16 September 2025 (UTC)

Note: WikiProject Chemistry has been notified of this discussion. veko. (user | talk | contribs) he/him 18:16, 25 September 2025 (UTC)