(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 -trimet hylhydrazino-1,3-butadiyne (7) can be prepared by simultaneous treatme nt of 3 with butyllithium and lithium diethylamide. The 4-butyl and 4- phenyl substituted (1,3-butadiynyl)hydrazines 9 are obtained by the re action of the corresponding 1,1-dichloro-1-buten-3-ynes 8 with two equ ivalents of lithium trimethylhydrazide. The reactivity of the new yneh ydrazine derivatives 3, 6 and 9 toward electron-deficient olefins 11 a nd the alpha-pyrone 13 is examined.