Helvetica Chimica Acta p. 1631 - 1637 (1983)
Update date:2022-07-30
Topics:
Staempfli, Urs
Galli, Roberto
Neuenschwander, Markus
The first synthesis of push-pull diacetylenes of type 1 is described.Reaction of perchlorobutyne (8) with two equivalents of dialkylamine, followed by dechlorination using two equivalents of butyllithium gives lithio-dialkylamino-diynes 7.Final acylation of these intermediates leads to push-pull diacetylenes 1b-1e in good yields.The method allows the introduction of both push and pull substituents in a simple one-pot-procedure.In addition, 1a is prepared by hydroxymethylation of lithio-morpholino-diyne 7c, followed by oxidation with manganese dioxide in acetone.
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