NDLI: Isoselenazolones as catalysts for the activation of bromine: bromolactonization of alkenoic acids and oxidation of alcohols.

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Isoselenazolones as catalysts for the activation of bromine: bromolactonization of alkenoic acids and oxidation of alcohols.

Content Provider	Semantic Scholar
Author	Balkrishna, Shah Jaimin Prasad, Ch Durga Panini, Piyush Detty, Michael R. Chopra, Deepak Kumar, S. P. Praveen
Copyright Year	2012
Abstract	Isoselenazolones were synthesized by a copper-catalyzed Se-N bond forming reaction between 2-halobenzamides and selenium powder. The catalytic activity of the various isoselenazolones was studied in the bromolactonization of pent-4-enoic acid. Isoselenazolone 9 was studied as a catalyst in several reactions: the bromolactonization of a series of alkenoic acids with bromine or N-bromosuccinimide (NBS) in the presence of potassium carbonate as base, the bromoesterification of a series of alkenes using NBS and a variety of carboxylic acids, and the oxidation of secondary alcohols to ketones using bromine as an oxidizing reagent. Mechanistic details of the isoselenazolone-catalyzed bromination reaction were revealed by (77)Se NMR spectroscopic and ES-MS studies. The oxidative addition of bromine to the isoselenazolone gives the isoselenazolone(IV) dibromide, which could be responsible for the activation of bromine under the reaction conditions. Steric effects from an N-phenylethyl group on the amide of the isoselenazolone and electron-withdrawing fluoro substituents on the benzo fused-ring of the isoselenazolone appear to enhance the stability of the isoselenazolone as a catalyst for the bromination reaction.
Starting Page	366
Ending Page	373
Page Count	8
File Format	PDF HTM / HTML
Alternate Webpage(s)	https://chm.iiserb.ac.in/pdf/publications/Publications_2012.pdf
PubMed reference number	23046286v1
Alternate Webpage(s)	https://doi.org/10.1021/jo301486c
DOI	10.1021/jo301486c
Journal	The Journal of organic chemistry
Volume Number	77
Issue Number	21
Language	English
Access Restriction	Open
Subject Keyword	Alkenes Amino Acids, Branched-Chain Bromine Bromosuccinimide Carbonates Carboxylic Acids Incisors, Fused Mandibular Ketone Measurement Reagents Selenium enzyme activity oxidation potassium carbonate secondary alcohols
Content Type	Text
Resource Type	Article

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