158050-40-9Relevant academic research and scientific papers
Synthesis and reactions of monosilylated 1,3,5-hexatriyne and 1,3,5,7-octatrayne. Total synthesis and caryoynencins
Yamaguchi,Park,Hirama,Torisu,Nakamura,Minami,Nishihara,Hiraoka
, p. 1717 - 1725 (2007/10/02)
Selective monodesilylation of 1,8-bis(t-butyldiphenylsilyl)-1,3,5,7-octatetrayne and 1,6-bis(t-butyldiphenylsilyl)-1,3,5-hexatriyne with lithiated phenylacetylene gave unstable 1-(t-butyldiphenylsilyl)-1,3,5,7-octatetrayne and 1-(t-butyldiphenylsilyl)-1,3,5-hexatriyne, respectively. The terminal acetylenes on lithiation added to aldehydes and a ketone giving polyynols in high yields. The reaction was applied to the synthesis of polyyne antibiotics, caryoynencins. Polymerization of the terminal octatetrayne on an ITO-coated glass plate gave a film, which showed conductivity of 10-4S cm-1 when doped with SO3.
