The preparation o cyano-carbonates and its application as acylanion equivalents

Abstract

Cyano carbonates, conveniently prepared in excellent yield by in situ trapping of cyanohydrin anions with chloroformates under phase transfer catalytic conditions, have been found to be efficient acyl-anion equivs. The alkylation of a-cyano carbonate afforded a convenient method for aldehyde-ketone conversion. E.g., alkylation of PhCH(CN)OCO2Et, obtained from PhCHO, with MeI gave 71% acetophenone.

Key words: GAS CHROMATOGRAPHY, INFRARED SPECTROPHOTOMETRY, CARBOXYLIC ACID ESTER, PHASE TRANSFER CATALYST, CARBONIC ACID P, ALCOHOL, PROTON MAGNETIC RESONANCE SPECTROMETRY, CYANOGEN COMPOUNDS, NUCLEOPHILIC REACTION, KETONE

CLC Number:

O621

Cite this article

CHEN ZUXING. The preparation o cyano-carbonates and its application as acylanion equivalents[J]. Chin. J. Org. Chem., 1990, 10(5): 445-447.

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