Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 80, Issue 17, Pages 8922-8928Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b01547
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- University Grant Commission, New Delhi
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A new series of alpha-functionalized trichloromethylcarbinols have been synthesized from corresponding alpha-halomethyl ketones, esters, and amides in 48-78% overall yields. Reactivity of nitrates obtained in the first step was dependent on the electron-withdrawing nature of the functional groups, and increases with increasing electron deficiency. Synthetic applications of such trichloromethylcarbinols for the preparation of chloromethyl-alpha-diketones, trichloromethylated dihydrofurans, and enol acetates of alpha-functionalized acid chlorides have been demonstrated. The reaction of these compounds in the Jocic-Reeve reaction was also demonstrated.
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