World Library  
Flag as Inappropriate
Email this Article

Prévost reaction

Article Id: WHEBN0014091260
Reproduction Date:

Title: Prévost reaction  
Author: World Heritage Encyclopedia
Language: English
Subject: Diol, Prevost, Woodward cis-hydroxylation
Collection:
Publisher: World Heritage Encyclopedia
Publication
Date:
 

Prévost reaction

The Prévost reaction is chemical reaction in which an alkene is converted by iodine and the silver salt of benzoic acid to a vicinal diol with anti stereochemistry.[1][2][3] The reaction was discovered by the French chemist Charles Prévost (1899-1983).

Reaction mechanism

The reaction between silver benzoate (1) and iodine is very fast and produces a very reactive iodinium benzoate intermediate (2). The reaction of the iodinium salt (2) with an alkene gives another short-lived iodinium salt (3). Nucleophilic substitution (SN2) by the benzoate salt gives the ester (4). Another silver ion causes the neighboring group substitution of the benzoate ester to give the oxonium salt (5). A second SN2 substitution by the benzoate anion gives the desired diester (6).

In the final step hydrolysis of the ester groups gives the anti-diol. This outcome is the opposite of that of the related Woodward cis-hydroxylation which gives syn addition.

References

See also

This article was sourced from Creative Commons Attribution-ShareAlike License; additional terms may apply. World Heritage Encyclopedia content is assembled from numerous content providers, Open Access Publishing, and in compliance with The Fair Access to Science and Technology Research Act (FASTR), Wikimedia Foundation, Inc., Public Library of Science, The Encyclopedia of Life, Open Book Publishers (OBP), PubMed, U.S. National Library of Medicine, National Center for Biotechnology Information, U.S. National Library of Medicine, National Institutes of Health (NIH), U.S. Department of Health & Human Services, and USA.gov, which sources content from all federal, state, local, tribal, and territorial government publication portals (.gov, .mil, .edu). Funding for USA.gov and content contributors is made possible from the U.S. Congress, E-Government Act of 2002.
 
Crowd sourced content that is contributed to World Heritage Encyclopedia is peer reviewed and edited by our editorial staff to ensure quality scholarly research articles.
 
By using this site, you agree to the Terms of Use and Privacy Policy. World Heritage Encyclopedia™ is a registered trademark of the World Public Library Association, a non-profit organization.
 



Copyright © World Library Foundation. All rights reserved. eBooks from Hawaii eBook Library are sponsored by the World Library Foundation,
a 501c(4) Member's Support Non-Profit Organization, and is NOT affiliated with any governmental agency or department.