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Synthese von ‘Push-Pull’-Diacetylenen

✍ Scribed by Urs Stämpfli; Roberto Galli; Markus Neuenschwander

Publisher
John Wiley and Sons
Year
1983
Tongue
German
Weight
457 KB
Volume
66
Category
Article
ISSN
0018-019X

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✦ Synopsis

Synthesis of ‘Push‐Pull’ Diacetylenes

The first synthesis of push‐pull diacetylenes of type 1 is described. Reaction of perchlorobutenyne (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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