S. Kashimura

Formation of a reasonably stabilized trichloromethyl anion by the reaction of chloroform with electrogenerated base, and its 1,4-addition to α,β-unsaturated carbonyl compounds

Abstract A reasonably stabilized trichloromethyl anion (TCMA) was formed by the reaction of chloroform with an electrogenerated base prepared by the electroreduction of 2-pyrrolidone, and the addition of this TCMA to α,β-unsaturated esters gave the corresponding β-trichloromethyl esters in good yields.

Anodic transformation of cycloheptatriene to tropone and tropolone

Abstract Cycloheptatriene (CHT) has been directly transformed to 7-methoxycycloheptatriene (7-MCHT), an equivalent compound to a tropylium salt, by the anodic oxidation of CHT in methanol. The further anodic oxidation of 3-MCHT prepared from 7-MCHT has been found to be an effective method of synthesis of tropone and tropolone.

Michael addition of novel acyl anion equivalents generated by the electroreduction of oxazolinium salts to activated olefins

Abstract Electroreduction of oxazolinium salts gave novel acyl anion equivalents (AAEs), and the Michael addition of these AAEs to activated olefins has been found to be promoted effectively by the addition of chlorotrimethylsilane into the reaction system. This reaction was applied to the synthesis of cis -jasmone and dihydrojasmone.

Electroinduced aldol condensation

Abstract Passing a catalytic amount of electricity (7.5 × 10 −3 F mol −1 ) into solution of aldehydes in DMF leads to formation of α, β-unsaturated carbonyl compounds through the aldol-type condensation with extremely high current efficiency (1 × 10 4 %).

ANODIC OXIDATION OF CYCLOHEPTATRIENE SYSTEMS AND ITS APPLICATION TO THE SYNTHESIS OF NON-BENZENOID AROMATIC COMPOUNDS

Abstract Anodic oxidation of cycloheptatrienes has been found to be one of the most powerful key tools for the preparation of a variety of non-benzenoid aromatic compounds such as tropylium salts, tropones, tropolones, 2H-cyclohepta[b]furan-2-ones, and azulenes.

Regioselective synthesis of substituted tropones and azulenes using anodic oxidation of cycloheptatriene systems as the key reaction

Abstract Regioselective synthesis of di- and trisubstituted tropones has been attained by utilizing anodic oxidation of cyclohepatatriene systems as the key reaction. This anodic oxidation has also been found to be useful for the regioselective synthesis of mono- and disubstituted azulenes.

A novel electroreductive alkylation of cycloheptatriene systems and its application to facile synthesis of β-thujaplicin☆

Abstract Electroreduction of cycloheptatriene or substituted cycloheptatrienes in the presence of an alkyl halide was found to be a unique and effective method for introducing regioselectively an alkyl group into seven-membered ring system and it was applied to a new synthesis of β-thujaplicin (hinokitiol).

Elongation of carbonyl compounds by utilizing electroreduction as a key step

Abstract The transformation of aldehydes, ketones and esters to the next higher homologous aldehydes was accomplished by utilizing electroreductive 1,2-elimination as a key step.