Volume 19, Issue 2
Heterocyclic Compounds
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ChemInform Abstract: Synthesis and Reactivity of Fluorinated Enynes.

F. TELLIER

F. TELLIER

Lab. Chim. Org., Univ. P. a. M. Curie, 75252 Paris, France

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R. SAUVETRE

R. SAUVETRE

Lab. Chim. Org., Univ. P. a. M. Curie, 75252 Paris, France

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J. F. NORMANT

J. F. NORMANT

Lab. Chim. Org., Univ. P. a. M. Curie, 75252 Paris, France

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First published: January 12, 1988

Abstract

Palladium-catalyzed cross-coupling reaction of the vinylic iodides (I) with the acetylides (II) yields the fluoroenynes (III).

ChemInform Abstract

Palladium-catalyzed cross-coupling reaction of the vinylic iodides (I) with the acetylides (II) yields the fluoroenynes (III). (IIId) and (IIIe) dimerize upon heating to form the cyclobutanes (IV). Treatment of (IIIe) with sulfuric acid leads to the formation of the fluoroallenic acid fluoride (V) and the lactones (VI) and (VII). Acidic hydrolysis of (IIIa) gives the α-fluoro-β-diketones (VIII) and the cyclic α-fluoro enones (IX).

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