TY - JOUR
T1 - A general synthetic method for 1,1'-bis(diacetylene-group)-connected ferrocene and π-electronic system
AU - Yoshino, Junro
AU - Shimizu, Rumi
AU - Hayashi, Naoto
AU - Higuchi, Hiroyuki
PY - 2011
Y1 - 2011
N2 - In contrast to the facile synthon ethynylferrocene for diacetylene ferrocene (Fc) derivatives, 1,1'-diethynylferrocene for the corresponding 1,1'-bis(diacetylene-group)-connected Fc derivatives is extremely difficult to handle under ordinary conditions, giving rise to spontaneous self-polymerization. Under modified Eglinton oxidative coupling conditions, it has been possible to generate 1,1'-diethynylferrocene in situ readily from a trimethylsilyl-protected precursor and to react it with other terminal acetylenes. The present tandem reactions could provide a general synthetic method for an extended π- electronic conjugation system of 1,1'-bis(diacetylene-group)-connected Fc derivatives, of which the chemistry has been scarcely developed.
AB - In contrast to the facile synthon ethynylferrocene for diacetylene ferrocene (Fc) derivatives, 1,1'-diethynylferrocene for the corresponding 1,1'-bis(diacetylene-group)-connected Fc derivatives is extremely difficult to handle under ordinary conditions, giving rise to spontaneous self-polymerization. Under modified Eglinton oxidative coupling conditions, it has been possible to generate 1,1'-diethynylferrocene in situ readily from a trimethylsilyl-protected precursor and to react it with other terminal acetylenes. The present tandem reactions could provide a general synthetic method for an extended π- electronic conjugation system of 1,1'-bis(diacetylene-group)-connected Fc derivatives, of which the chemistry has been scarcely developed.
UR - http://www.scopus.com/inward/record.url?scp=78751510161&partnerID=8YFLogxK
U2 - 10.1246/bcsj.20100252
DO - 10.1246/bcsj.20100252
M3 - 学術論文
AN - SCOPUS:78751510161
SN - 0009-2673
VL - 84
SP - 110
EP - 118
JO - Bulletin of the Chemical Society of Japan
JF - Bulletin of the Chemical Society of Japan
IS - 1
ER -