Volume 20, Issue 2
Isocyclic Compounds
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ChemInform Abstract: Acylamidation of Acetylenes.

I. D. GRIDNEV

I. D. GRIDNEV

Inst. Org. Chem. Biochem., Univ. Bonn, D-5300 Bonn 1

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E. S. BALENKOVA

E. S. BALENKOVA

Inst. Org. Chem. Biochem., Univ. Bonn, D-5300 Bonn 1

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First published: January 10, 1989

Abstract

The reaction between the alkynes (I), the nitriles (II) and acetyl tetrafluoroborate (III) proceeds regio- and stereospecifically by way of a syn-addition according to Markovnikov to afford the hitherto unknown Z-configurated N-acyl-β-amino-α,β-unsaturated ketones (III).

ChemInform Abstract

The reaction between the alkynes (I), the nitriles (II) and acetyl tetrafluoroborate (III) proceeds regio- and stereospecifically by way of a syn-addition according to Markovnikov to afford the hitherto unknown Z-configurated N-acyl-β-amino-α,β-unsaturated ketones (III). The Z configuration is unambiguously deduced from their IR spectra. Furthermore, these novel compounds are characterized by a strong intramolecular hydrogen bond.

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