Reactions of Electrochemically Generated Alkoxy Phosphonium Ions
Reactions of alkoxy triphenylphosphonium salts (1), prepared by a simple electrochemical procedure from primary and secondary alcohols, with nucleophiles indicated that a soft nucleophile is apt to attack at the α -carbon to give the corresponding Sn2 product, while a hard one at the phosphorus atom to regenerate the original alcohol. Thermal decomposition of 1 with BF4 - as counter anion has been shown to afford alkyl fluorides. One-pot dehydroxysubstitution reactions at the anomeric carbons of protected sugars has been effected via in situ decomposition of the corresponding electrochemically generated alkoxy phosphonium ions.
KeywordsSecondary Alcohol Tertiary Alcohol Phosphonium Salt Anomeric Carbon Undivided Cell
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