(1,3-BUTADIYNYL)HYDRAZINES - A NEW CLASS OF ELECTRON-RICH ALKADIYNES

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-but...

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Bibliographic Details
Published inSynthesis (Stuttgart) no. 4; pp. 383 - 386
Main Authors LOFFLER, A, HIMBERT, G
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 1994
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
PERCHLOROBUTENYNE
N-N',N'-TRIMETHYL-N-(TRICHLORO-3-BUTEN-1-YNYL)HYDRAZINE
N-(BUTADIYNYL)HYDRAZINE DERIVATIVES
YNAMINES
CYCLOADDITIONS
1,1-DICHLORO-1-ALKEN-3-YNES
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Summary: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-1-buten-3-ynes 8 with two equivalents of lithium trimethylhydrazide. The reactivity of the new ynehydrazine derivatives 3, 6 and 9 toward electron-deficient olefins 11 and the alpha-pyrone 13 is examined.
ISSN:0039-7881
DOI:10.1055/s-1994-25482