Abstract
Aryl disubstituted diacetylenes with spacers of different lengths (CH 2 O, CH 2 OCH 2 CH 2 O, and CH 2 OCH 2 CH 2 CH 2 O) have been synthesized. Smaller homologues of the series were readily obtained by nucleophilic substitutions on 2,4-hexadiynylene bis(p-toluenesulfonate). 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
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