TY - JOUR
T1 - Synthesis and reactions of monosilylated 1,3,5-hexatriyne and 1,3,5,7-octatrayne. Total synthesis and caryoynencins
AU - Yamaguchi, M.
AU - Park, H. J.
AU - Hirama, M.
AU - Torisu, K.
AU - Nakamura, S.
AU - Minami, T.
AU - Nishihara, H.
AU - Hiraoka, T.
PY - 1994/8/25
Y1 - 1994/8/25
N2 - 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.
AB - 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.
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U2 - 10.1246/bcsj.67.1717
DO - 10.1246/bcsj.67.1717
M3 - Article
AN - SCOPUS:0027965797
VL - 67
SP - 1717
EP - 1725
JO - Bulletin of the Chemical Society of Japan
JF - Bulletin of the Chemical Society of Japan
SN - 0009-2673
IS - 6
ER -