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Carbanions of 1,3-Dithianes. Reagents for CC Bond Formation by Nucleophilic Displacement and Carbonyl Addition

✍ Scribed by Prof. Dr. E. J. Corey; Dr. D. Seebach

Publisher: John Wiley and Sons
Year: 1965
Tongue: English
Weight: 336 KB
Volume: 4
Category: Article
ISSN: 0044-8249
DOI: 10.1002/anie.196510752

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✦ Synopsis

H2S04 a t 0°C. Heating a drop in a test tube over a free flame leads to detonation; sensitivity to shock is notable only after admixture of a few grains of sand. Addition of bromine affords 2,3-dibromopropyl hydroperoxide (solvent: ether; Br2 added dropwise at 15 "C). The isomer, 2-bromo-1-bromomethylethyl hydroperoxide, was recently 141 obtained by simultaneous action of oxygen and bromine on ally1 bromide. Addition of chlorine to compound ( I ) is also possible. The hydroperoxide ( I ) is perhaps an intermediate product of the oxygenation of propene to acroleinC51 or glycerol[6l. In accord with this suggestion acrolein can be detected on thermal decomposition of compound ( I ) .

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