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A versatile synthesis of 2-haloalk-2(Z)-en-1-ols and 1-chloro-1(Z)-alkenes from trichloromethylcarbinols

โœ Scribed by Rachid Baati; D.K Barma; J.R Falck; Charles Mioskowski

Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
59 KB
Volume
43
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

CrCl 2 converts trichloromethylcarbinols under mild conditions to (E)-a-haloalkylidene chromium carbenoids which add to aldehydes or are quenched with water affording 2-haloalk-2(Z)-en-1-ols and 1-chloro-1(Z)-alkenes, respectively, in high yield.

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โœ Rachid Baati; D.K. Barma; U.Murali Krishna; Charles Mioskowski; J.R. Falck ๐Ÿ“‚ Article ๐Ÿ“… 2002 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 70 KB

Mild, room temperature CrCl 2 reduction of 1,1,1-trichloroalkanes stereoselectively generates (Z)-1-chloro-2-substituted-1-alkenes in excellent yields.

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Three-component synthesis of 2-haloalk-2(Z)-en-1-ols via tandem haloalkylidenationโ€“aldehyde addition
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Cr(II)-induced condensation of CCl 4 or CBr 4 with an aldehyde stereospecifically generates an (E)-a-haloalkylidene chromium carbenoid which adds in situ to a second equivalent of aldehyde furnishing 2-haloalk-2(Z)-en-1-ols in high yield.