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A facile one-pot synthesis of alpha-bromo-alpha,beta-unsaturated esters from alcohols. 2010

Usama Karama, and Zeid Al-Othman, and Abdullah Al-Majid, and Abdulrahman Almansour
Chemistry Department, College of Science, King Saud University, P.O. Box 2455 Riyadh 11451, Saudi Arabia. Karama@ksu.edu.sa

Treatment of N-bromosuccinimide (NBS) with (carboethoxymethylene) triphenylphosphorane (1) in CH(2)Cl(2) followed by the addition of an alcohol in the presence of manganese dioxide under ultrasonic irradiation constitutes a stereoselective one-pot procedure for the preparation of Z-configured alpha-bromo-alpha,beta-unsaturated esters in good to excellent yield.

UI MeSH Term Description Entries
D008722 Methods A series of steps taken in order to conduct research. Techniques,Methodological Studies,Methodological Study,Procedures,Studies, Methodological,Study, Methodological,Method,Procedure,Technique
D010753 Phosphoranes Inorganic or organic compounds that contain pentavalent phosphorus and the general formula R5P.
D001974 Bromosuccinimide A brominating agent that replaces hydrogen atoms in benzylic or allylic positions. It is used in the oxidation of secondary alcohols to ketones and in controlled low-energy brominations. (From Miall's Dictionary of Chemistry, 5th ed; Hawley's Condensed Chemical Dictionary, 12th ed,). Succinbromimide,N-Bromosuccinimide,N Bromosuccinimide
D004952 Esters Compounds derived from organic or inorganic acids in which at least one hydroxyl group is replaced by an –O-alkyl or another organic group. They can be represented by the structure formula RCOOR’ and are usually formed by the reaction between an acid and an alcohol with elimination of water. Ester
D000438 Alcohols Alkyl compounds containing a hydroxyl group. They are classified according to relation of the carbon atom: primary alcohols, R-CH2OH; secondary alcohols, R2-CHOH; tertiary alcohols, R3-COH. (From Grant & Hackh's Chemical Dictionary, 5th ed)
D013237 Stereoisomerism The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer
D014465 Ultrasonics A subfield of acoustics dealing in the radio frequency range higher than acoustic SOUND waves (approximately above 20 kilohertz). Ultrasonic radiation is used therapeutically (DIATHERMY and ULTRASONIC THERAPY) to generate HEAT and to selectively destroy tissues. It is also used in diagnostics, for example, ULTRASONOGRAPHY; ECHOENCEPHALOGRAPHY; and ECHOCARDIOGRAPHY, to visually display echoes received from irradiated tissues. Ultrasonic

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