Comments on: Gilman Reagents (Organocuprates): What They’re Used For https://www.masterorganicchemistry.com/2016/02/05/gilman-reagents-organocuprates-what-theyre-used-for/ Thu, 06 Jul 2023 19:18:36 +0000 hourly 1 https://wordpress.org/?v=6.6.2 By: James Ashenhurst https://www.masterorganicchemistry.com/2016/02/05/gilman-reagents-organocuprates-what-theyre-used-for/#comment-643793 Mon, 05 Dec 2022 15:54:09 +0000 https://www.masterorganicchemistry.com/?p=9658#comment-643793 In reply to AH.

Still works! Plenty of examples in this volume: https://onlinelibrary.wiley.com/doi/abs/10.1002/0471264180.or041.02

]]> By: AH https://www.masterorganicchemistry.com/2016/02/05/gilman-reagents-organocuprates-what-theyre-used-for/#comment-643677 Sat, 03 Dec 2022 14:08:51 +0000 https://www.masterorganicchemistry.com/?p=9658#comment-643677 What happens if there is already an R group on the beta carbon?

]]> By: James Ashenhurst https://www.masterorganicchemistry.com/2016/02/05/gilman-reagents-organocuprates-what-theyre-used-for/#comment-640671 Thu, 20 Oct 2022 10:11:13 +0000 https://www.masterorganicchemistry.com/?p=9658#comment-640671 In reply to Jonathan.

Primary alkyl sulfonates work well. SN2 reactions between Gilman reagents and secondary alkyl sulfonates don’t work well. For that matter there are not many good examples of organocuprates reacting with secondary alkyl halides or tosylates.
https://pubs.acs.org/doi/pdf/10.1021/ja00804a039

]]> By: Jonathan https://www.masterorganicchemistry.com/2016/02/05/gilman-reagents-organocuprates-what-theyre-used-for/#comment-640582 Tue, 18 Oct 2022 21:26:46 +0000 https://www.masterorganicchemistry.com/?p=9658#comment-640582 Beyond acid chlorides, will Gilman reagents add to alkylsulfonyl chlorides like MsCl? I don’t have access to SciFinder or Reaxys and am having a hard time checking to see whether this would be a valid reaction.

]]> By: Best 13 Choose Reagents To Convert 2-cyclohexenone To The Following Compounds. - Vik News https://www.masterorganicchemistry.com/2016/02/05/gilman-reagents-organocuprates-what-theyre-used-for/#comment-638451 Mon, 19 Sep 2022 18:54:57 +0000 https://www.masterorganicchemistry.com/?p=9658#comment-638451 […] Quote from the source: … […]

]]> By: James Ashenhurst https://www.masterorganicchemistry.com/2016/02/05/gilman-reagents-organocuprates-what-theyre-used-for/#comment-635377 Mon, 15 Aug 2022 19:47:11 +0000 https://www.masterorganicchemistry.com/?p=9658#comment-635377 In reply to Tirth bhayani.

I don’t think I understand your question. What reaction are you thinking of doing with organocuprates?

]]> By: Tirth bhayani https://www.masterorganicchemistry.com/2016/02/05/gilman-reagents-organocuprates-what-theyre-used-for/#comment-635206 Sat, 13 Aug 2022 06:27:02 +0000 https://www.masterorganicchemistry.com/?p=9658#comment-635206 Hey there, First of all amazing content up there. I am Tirth from India preparing for JEE. I have this doubt in the comparision of leaving group strength which you said. If organocuprate is going from more stability to less stability, it will not tend to perfom that reaction. Then shouldn’t it be less nucleophilic?

]]> By: James Ashenhurst https://www.masterorganicchemistry.com/2016/02/05/gilman-reagents-organocuprates-what-theyre-used-for/#comment-623809 Fri, 01 Apr 2022 19:36:30 +0000 https://www.masterorganicchemistry.com/?p=9658#comment-623809 In reply to Joey.

Fixed, thanks

]]> By: James Ashenhurst https://www.masterorganicchemistry.com/2016/02/05/gilman-reagents-organocuprates-what-theyre-used-for/#comment-623806 Fri, 01 Apr 2022 18:50:16 +0000 https://www.masterorganicchemistry.com/?p=9658#comment-623806 In reply to Joey.

Thank you!

]]> By: Joey https://www.masterorganicchemistry.com/2016/02/05/gilman-reagents-organocuprates-what-theyre-used-for/#comment-623801 Fri, 01 Apr 2022 17:35:29 +0000 https://www.masterorganicchemistry.com/?p=9658#comment-623801 the DOI is correct but the hyperlink is wrong

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