Synthesis of a Series of Symmetrically Disubstituted Diacetylenes with Polychlorophenyl Rings as Side Groups and Linear Polyether Chains as Spacers

Esteve Hernàndez; Angels Galan; Concepció Rovira; Jaume Veciana

doi:10.1055/s-1992-26327

Synthesis 1992; 1992(11): 1164-1169
DOI: 10.1055/s-1992-26327

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Synthesis of a Series of Symmetrically Disubstituted Diacetylenes with Polychlorophenyl Rings as Side Groups and Linear Polyether Chains as Spacers

Esteve Hernàndez^* , Angels Galan, Concepció Rovira, Jaume Veciana

^*Institut de Ciència de Materials de Barcelona (CSIC), Campus de la U. A. B, E-08193 Bellaterra, Spain

Abstract

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Aryl disubstituted diacetylenes with spacers of different lengths (CH₂O, CH₂OCH₂CH₂O, and CH₂OCH₂CH₂CH₂O) have been synthesized.Smaller homologues of the series were readily obtained by nucleophilic substitutions on 2,4-hexadiynylene bis(p-toluenesul-fonate). However higher homologues could not be prepared by this method from the corresponding extended bistosylates due to their low reactivities. The observed decrease of reactivity with phenoxides of such extended bistosylates is ascribed to folded conformations adopted by these derivatives. Consequently, the synthesis of higher members of the series was carried out by a multistep procedure involving appropriately functionalized monoacetylenes.

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