Literature DB >> 16623545

A new specific mechanism for the acid catalysis of the addition step in the Baeyer-Villiger rearrangement.

J Raúl Alvarez-Idaboy1, Lino Reyes, Julián Cruz.   

Abstract

[structure: see text] A new transition state of the addition step in the Baeyer-Villiger reaction was found. The role of proton acceptor is played by the carbonyl oxygen atom, and the free energy barrier is 12.7 kcal/mol lower than that previously reported. This finding changes the mechanism for the acid catalysis and could be of interest for similar reactions in which it is known that such catalysis occurs, especially in nonpolar solvents.

Entities:  

Year:  2006        PMID： 16623545     DOI： 10.1021/ol060261z

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  5 in total

1.  A theoretical and experimental evaluation of imidazolium-based ionic liquids for atmospheric mercury capture.

Authors:  Cristina Iuga; Corina Solís; J Raúl Alvarez-Idaboy; Miguel Angel Martínez; Ma Antonieta Mondragón; Annik Vivier-Bunge
Journal:  J Mol Model       Date:  2014-04-15       Impact factor: 1.810

2.  Synthesis of (R)-2-(benzyloxy)-tetrahydro-5,5-dimethylfuran by a new oxidative rearrangement.

Authors:  David Díez; Marta G Nuñez; Rosalina F Moro; Narciso M Garrido; Isidro S Marcos; Pilar Basabe; Julio G Urones
Journal:  Molecules       Date:  2006-12-18       Impact factor: 4.411

3.  Overriding Traditional Electronic Effects in Biocatalytic Baeyer-Villiger Reactions by Directed Evolution.

Authors:  Guangyue Li; Marc Garcia-Borràs; Maximilian J L J Fürst; Adriana Ilie; Marco W Fraaije; K N Houk; Manfred T Reetz
Journal:  J Am Chem Soc       Date:  2018-08-13       Impact factor: 15.419

4.  ROS initiated oxidation of dopamine under oxidative stress conditions in aqueous and lipidic environments.

Authors:  Cristina Iuga; J Raul Alvarez-Idaboy; Annik Vivier-Bunge
Journal:  J Phys Chem B       Date:  2011-10-04       Impact factor: 2.991

5.  Mechanistic and chiroptical studies on the desulfurization of epidithiodioxopiperazines reveal universal retention of configuration at the bridgehead carbon atoms.

Authors:  Fanny L Cherblanc; Ya-Pei Lo; Wouter A Herrebout; Patrick Bultinck; Henry S Rzepa; Matthew J Fuchter
Journal:  J Org Chem       Date:  2013-11-08       Impact factor: 4.354
  5 in total

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