1987 Fiscal Year Final Research Report Summary

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

Research Project

Project/Area Number	61550640
Research Category	Grant-in-Aid for General Scientific Research (C)
Allocation Type	Single-year Grants
Research Field	Synthetic chemistry
Research Institution	Okayama University, Faculty of engineering
Principal Investigator	UNEYAMA Kenji Okayama University, Faculty of Enculty of Engineering, Professor, 工学部, 教授 (00033150)
Project Period (FY)	1986 – 1987
Keywords	Zero-valent tin / ヒドロキシメチル化 / アルドール反応 / 活性スズ試薬
Research Abstract	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, namely 1) Tin-promoted electrochemical hydrodimerization of ionones 2) SnCl_2-promoted -exomethylenelactonization of bromomethylacrylic acid with alhdeydes in an MeOCH_2CH_2OH-H_2O-AcoH system 3) Al-SnCl_2-promoted hydroxymethylation of allyl chlorides in aqueous THF 4) Al -SnCl_2-promoted stereocontrolled aldol reaction of -bromoketones with aldehydes in dry DMF in the presence of a catalytic amount of acetic acid The 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.

(3 results)