The thermal rearrangement of 1, 5-hexadiyne and related compounds

WD Huntsman, HJ Wristers

Index: Huntsman,W.D.; Wristers,H.J. Journal of the American Chemical Society, 1967 , vol. 89, # 2 p. 342 - 347

Full Text: HTML

Citation Number: 66

Abstract

Abstract: 1, 5-Alkadiynes undergo intramolecular rearrangement at elevated temperatures to give dimethylenecyclobutenes. Thus, at 335 O in a flow system, 1, 5-hexadiyne rearranges rapidly to 3, 4-dimethylenecyclobutene. 1, 5-Heptadiyne rearranges somewhat more slowly, giving l-methyl-3, 4-dimethylenecyclobutene at 377 O, while 1, 2-dimethyl-3, 4- dimethylenecyclobutene is formed from 2, 6-octadiyne at 410". Evidence pertinent to the ...