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

Shoji Hara, Hidetaka Dojo, Tatuo Kato, Akira Suzuki

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Abstract

Abstract Lithium acetylides with functional groups such as orthoester or acetal group in the molecule 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.

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Abstract Lithium acetylides with functional groups such as orthoester or acetal group in the molecule 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.

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Available abstract

Abstract Lithium acetylides with functional groups such as orthoester or acetal group in the molecule 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.

Key concepts: Chemistry, Acetal, Orthoester, Lithium (medication), Organic chemistry, Alkoxy group, Alkyl, Medicinal chemistry

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