Comments on: Elimination of Alcohols To Alkenes With POCl3 https://www.masterorganicchemistry.com/2015/04/28/elimination-of-alcohols-to-alkenes-with-pocl3/ Sat, 01 Jun 2024 12:40:40 +0000 hourly 1 https://wordpress.org/?v=6.6.2 By: James Ashenhurst https://www.masterorganicchemistry.com/2015/04/28/elimination-of-alcohols-to-alkenes-with-pocl3/#comment-695473 Sat, 01 Jun 2024 12:40:40 +0000 https://www.masterorganicchemistry.com/?p=8901#comment-695473 In reply to Madhav Mittal.

Of course there is. Check the first reference.

https://pubs.acs.org/doi/10.1021/ja01527a028

https://pubs.acs.org/doi/pdf/10.1021/jo00263a020

]]> By: James Ashenhurst https://www.masterorganicchemistry.com/2015/04/28/elimination-of-alcohols-to-alkenes-with-pocl3/#comment-695472 Sat, 01 Jun 2024 12:38:08 +0000 https://www.masterorganicchemistry.com/?p=8901#comment-695472 In reply to Madhav Mittal.

Pyridine isn’t a particularly strong base, but it will perform elimination (E2) reactions when the leaving group is good enough, such as OMs or OTs. This includes the leaving created when POCl3 reacts with alcohols.

]]> By: Madhav Mittal https://www.masterorganicchemistry.com/2015/04/28/elimination-of-alcohols-to-alkenes-with-pocl3/#comment-695466 Sat, 01 Jun 2024 11:15:04 +0000 https://www.masterorganicchemistry.com/?p=8901#comment-695466 My instructor says that there is no such reaction of alcohols with POCL3!
Can you please tell an international reference book in which this reaction might be given.

]]> By: Madhav Mittal https://www.masterorganicchemistry.com/2015/04/28/elimination-of-alcohols-to-alkenes-with-pocl3/#comment-695323 Fri, 31 May 2024 07:40:24 +0000 https://www.masterorganicchemistry.com/?p=8901#comment-695323 When treating 3 degree alcohol with POCL3, we get a 3 degree alkyl chlorophosphateester , and if we are adding pyridine which we would consider a weak base ( according to Quick N Dirty Guide for SN1/SN2/E1/E2 , because it is neutral),so should E1 pathway not dominate in this case?

]]> By: CHANDRU https://www.masterorganicchemistry.com/2015/04/28/elimination-of-alcohols-to-alkenes-with-pocl3/#comment-686122 Tue, 27 Feb 2024 22:45:55 +0000 https://www.masterorganicchemistry.com/?p=8901#comment-686122 how this is different from transforming alcohols to tosylates in presence of pyridine ?

]]> By: DM https://www.masterorganicchemistry.com/2015/04/28/elimination-of-alcohols-to-alkenes-with-pocl3/#comment-631195 Thu, 23 Jun 2022 18:30:49 +0000 https://www.masterorganicchemistry.com/?p=8901#comment-631195 Typo: in the second step of the mechanism, pyridine removes a proton (arrow shifted).

]]> By: James Ashenhurst https://www.masterorganicchemistry.com/2015/04/28/elimination-of-alcohols-to-alkenes-with-pocl3/#comment-627799 Thu, 19 May 2022 19:57:58 +0000 https://www.masterorganicchemistry.com/?p=8901#comment-627799 In reply to Miracle uche.

If by alkanol you mean, alcohol, no. They are at the wrong oxidation state.

]]> By: Miracle uche https://www.masterorganicchemistry.com/2015/04/28/elimination-of-alcohols-to-alkenes-with-pocl3/#comment-627142 Tue, 10 May 2022 10:03:03 +0000 https://www.masterorganicchemistry.com/?p=8901#comment-627142 Can we react alkanols with strong acids to give an ester product

]]> By: James Ashenhurst https://www.masterorganicchemistry.com/2015/04/28/elimination-of-alcohols-to-alkenes-with-pocl3/#comment-615319 Tue, 07 Dec 2021 18:41:29 +0000 https://www.masterorganicchemistry.com/?p=8901#comment-615319 In reply to Bob Hanson.

That’s a great point to look into, Bob. Thank you.

]]> By: James Ashenhurst https://www.masterorganicchemistry.com/2015/04/28/elimination-of-alcohols-to-alkenes-with-pocl3/#comment-615292 Tue, 07 Dec 2021 04:21:16 +0000 https://www.masterorganicchemistry.com/?p=8901#comment-615292 In reply to Khanh.

Certainly not a large base. A more sterically hindered base related to pyridine would be 2,4,6-collidine, or even better, 2,6-di-t-butyl 4 methyl pyridine.

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