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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
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Publication History

Publication Date:
17 September 2002 (online)

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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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