Template:Did you know nominations/Bis(cyclopentadienyl)titanium(III) chloride


 * The following is an archived discussion of the DYK nomination of the article below. Please do not modify this page. Subsequent comments should be made on the appropriate discussion page (such as |this nomination's talk page, the article's talk page or Wikipedia talk:Did you know), unless there is consensus to re-open the discussion at this page. No further edits should be made to this page.

The result was: promoted by Cwmhiraeth (talk) 05:52, 30 June 2017 (UTC)

Bis(cyclopentadienyl)titanium(III) chloride

 * ... that the Nugent–RajanBabu reagent can be used to effect the Barbier, McMurry, Michael, and pinacol coupling reactions?
 * ALT1:... that the Nugent–RajanBabu reagent can be used in the synthesis of vinorelbine, which is used in treating non-small-cell lung cancer?
 * ALT2:... that vinorelbine, used to treat non-small-cell lung cancer, can be prepared using the Nugent–RajanBabu reagent?
 * Reviewed: Template:Did you know nominations/Muscle Dysmorphia
 * Comment: Mcfliz is a new editor, having only edited draft and article space to create this new article plus commons edits for new diagrams associated with it. It was created by Mcfliz through the AfC process, moved to mainspace by Graeme Bartlett on 22 April, then there was a cut-and-paste moved by Smokefoot which Graeme repaired.  This nomination is a little beyond the 7 day mark, but the work is an impressive new article (3720 characters of readable prose, 520 words, 7 images, 24 references) so I want to encourage McFliz with some main page attention.  I need to do some work on the article (hopefully within 24 hours) to support ALT1 and ALT2, there are ample sources available.  Now done. EdChem (talk) 08:27, 5 May 2017 (UTC)
 * References:
 * That the bis(cyclopentadienyl)titanium(III) chloride is also known as the Nugent–RajanBabu reagent: and.
 * That it can be used with Barbier reaction and pinacol coupling reaction:.
 * That it can be used with Michael addition and the McMurry reaction.
 * Synthesis from leurosine to anhydrovinblastine and on to vinorelbine  – this reference also confirms use with non-small-cell lung cancer, as does.

Moved to mainspace by Mcfliz (talk). Nominated by EdChem (talk) at 23:53, 1 May 2017 (UTC).


 * Symbol question.svg New and long enough, within policy, Earwig detects to copyvios, QPQ done. Scheme 13 of  uses a different synthetic route to anhydrovinblastine than, which doesn't use the Nugent–RajanBabu reagent.  Technically the hooks are still correct since it "can be" synthesized that way, but it would be better to show that the reagent is routinely used in that synthesis, especially commercially.  Alternatively, is is possible to make a hook more accessible to laymen?  How would you describe what reactions this reagent can do that can be done no other way?  Antony–22 (talk⁄contribs) 21:24, 11 May 2017 (UTC)
 * Pinging. Antony–22 (talk⁄contribs) 09:34, 17 May 2017 (UTC)


 * Symbol possible vote.svg It has been a month since this was originally reviewed, and nearly four weeks since the nominator was first pinged; action is needed soon if this is to continue. The nominator has again been notified on his talk page; I hope a response is made shortly. BlueMoonset (talk) 04:43, 11 June 2017 (UTC)
 * As I noted, the hooks are technically true, though perhaps less interesting than they seem at first glance. I'm hoping for an improved hook, but I could approve these as well.  Antony–22 (talk⁄contribs) 22:52, 14 June 2017 (UTC)
 * I have struck the original hook as far too inaccessible; the two ALTs, with their mention of a treatment for cancer, have at least something to get the attention of the average reader. EdChem, might you be able to come up with something more accessible still, or otherwise address Antony-22's original comments? Antony-22, if EdChem hasn't responded in the next 48 hours, I think it's time to decide whether the ALT hooks are sufficiently interesting, and give them a final icon. Many thanks. BlueMoonset (talk) 13:37, 19 June 2017 (UTC)

"Doris and co-workers reported in 2002 the Cp2TiCl-mediated deoxigenation of the alkaloid leurosine (from Catharantus roseus), leading to anhydrovinblastine (Scheme 30), the key intermediate in the symthesis of the anticancer drug navelbine"
 * Comment. I'm not sure that I follow why Antony-22 needs to qualify the hook(s) as technically correct. Either the substance can be sythesised that way, in which case the hook is correct without qualification and is good to go, or it can't and should be struck.  I don't see the need to prove that it is routinely done that way.  However, to attempt to resolve this, "New Advances in Titanium-Mediated Free Radical Reactions" opens with "Titanium complexes have been widely used as catalysts for C-C bond-forming processes via free-radical routes."  This is behind a paywall, but a snippet from gscholar leads me to believe that the subject process of the hook is one such process;
 * I believe that "Cp2TiCl" is a synonym for Nugent–RajanBabu reagent and "navelbine" is a synonym for vinorelbine thus providing the asked for verification. SpinningSpark 17:39, 19 June 2017 (UTC)


 * I have made some changes that I hope clarifies things. Approaches to vinorelbine are (1) vindoline + catharanthine  (both from the Periwinkle) to anhydrovinblastine or (2) leurosine (also from the Periwinkle) with N-RB reagent to anhydrovinblastine, in either case then used to make vinorelbine.  EdChem (talk) 13:23, 20 June 2017 (UTC)  PS: I have added the quote from the Molecules reference above that anhydrovinblastine "can be considered as the key intermediate for the synthesis of vinorelbine." (, page 5905).  This opens the way for another alt, like:
 * ALT3a:... that anhydrovinblastine, the key intermediate in the synthesis of non-small-cell lung cancer agent vinorelbine, can be prepared using the Nugent–RajanBabu reagent?
 * ALT3b:... the Nugent–RajanBabu reagent can be used to prepare a key intermediate in the synthesis of vinorelbine, a treatment for non-small-cell lung cancer?
 * Thoughts? EdChem (talk) 03:56, 21 June 2017 (UTC)
 * File:Vinorelbine from leurosine and from catharanthine plus vindoline.jpg highlights the relationships, FYI. EdChem (talk) 05:31, 21 June 2017 (UTC)
 * Sorry for the delay. I'll take a look at this in the next few days.  Antony–22 (talk⁄contribs) 04:56, 22 June 2017 (UTC)
 * Symbol confirmed.svg ALT3a and ALT3b are fine with me. I've slightly tightened 3b, which is preferred.  Antony–22 (talk⁄contribs) 06:20, 29 June 2017 (UTC)