Preparation and Diels-Alder reactivity of several new chalcogen-halogen substituted butadienes

AJ Bridges, JW Fischer

Index: Bridges, Alexander J.; Fischer, John W. Journal of Organic Chemistry, 1984 , vol. 49, # 16 p. 2954 - 2961

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Citation Number: 24

Abstract

Addition of halogens and pseudohalogens across one*-bond of 1, 4-dichlorobut-2-yne, followed by a 1, 4-elimination, is an efficient synthesis of several new polysubstituted butadienes. If the product dienes have a sulfur or selenium substitutent they are quite reactive, undergoing cycloaddition with the moderately reactive dienophile methyl vinyl ketone at 20 OC in the presence of boron trifluoride etherate. The regiochemistry of the ...