THE REACTION OF TRIALKYLBORANES WITH LITHIUM ACETYLIDES PREPARED FROM TRIETHYL ORTHOPROPIOLATE AND PROPIOLALDEHYDE DIETHYL ACETAL

Article abstract of DOI:10.1246/cl.1983.1125

Lithium acetylides with functional groups such as orthoester or acetal group in the molecula react with trialkylboranes with the migration of alkyl groups.The oxidation of the intermediates obtained from triethyl orthopropiolate gives a mixture of β-hydroxy- and α,β-unsaturated esters, and the oxidation of those from propiolaldehyde diethyl acetal gives (E)-1-ethoxy-1-alken-3-ones respectively.