Organic Synthesis by the Use of the Electrochemically Generated Active Zero-valent Tin Reagent

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The generation and recycle use of the active zero-valent tin reagent have been investigated by the electroreduction and aluminum-promoted reduction.Four types of reactions ahbeen examined, namely1) Tin-promoted electrochemical hydrodimerization of ionones2) SnCl_2-promoted -exomethylenelactonization of bromomethylacrylic acid with alhdeydes in an MeOCH_2CH_2OH-H_2O-AcoH system3) Al-SnCl_2-promoted hydroxymethylation of allyl chlorides in aqueous THF4) Al -SnCl_2-promoted stereocontrolled aldol reaction of -bromoketones with aldehydes in dry DMF in the presence of a catalytic amount of acetic acidThe zero-valent tin generated by Al-SnCl_2 system was found to be markedly active so that the reagent can insert to cinamyl chloride in aqueous solution without hydrolysis of the cinnamyl chloride.