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Synthesis 1994; 1994(4): 383-386
DOI: 10.1055/s-1994-25482
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(1,3-Butadiynyl)hydrazines: A New Class of Electron-Rich Alkadiynes

Achim Löffler* , Gerhard Himbert
  • *Fachbereich Chemie der Universität Kaiserslautern, Postfach 3049, D-67653 Kaiserslautern, Germany
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Publication Date:
17 September 2002 (online)

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3,4,4-Trichloro-1-trimethylhydrazino-3-buten-1-yne (3), obtained from perchlorobutenyne (1) and trimethylhydrazine (2) forms the novel (1,3-butadiynyl)hydrazines 6 by consecutive treatment with butyllithium and various electrophiles. On the other hand the 4-diethylamino-1-trimethylhydrazino-1,3-butadiyne (7) can be prepared by simultaneous treatment of 3 with butyllithium and lithium diethylamide. The 4-butyl and 4-phenyl substituted (1,3-butadiynyl)hydrazines 9 are obtained by the reaction of the corresponding 1,1-dichloro-l-buten-3-ynes 8 with two equivalents of lithium trimethylhydrazide. The reactivity of the new ynehydrazine derivatives 3,6and 9 toward electron-deficient olefins 11 and the α-pyrone 13 is examined.