Hydride-induced novel cyclization of dienedinitriles leading to multifunctionalized cyclopentadienes.
By treatment with LiAlH(4), 1,4-dicyano-1,4-bis(trimethylsilyl)-1,3-dienes underwent a novel hydride-induced nucleophilic intermolecular 1,4-addition to the alpha,beta-unsaturated nitrile moiety, followed by an immediate nucleophilic intramolecular 1,2-addition to the remaining CN group, to afford multiply functionalized cyclopentadienes in high isolated yields. These multifunctional (-CN, -NH(2), -SiMe(3), -H) cyclopentadienes are of a rich and interesting reaction chemistry as preliminarily demonstrated by their reaction with ArNCO involving both the substituent and the ring.
Zhang
Hui-Jun
HJ
Beijing National Laboratory for Molecular Science, College of Chemistry, Peking University, Beijing 100871, China.
Meng
Tianhao
T
Demerseman
Bernard
B
Bruneau
Christian
C
Xi
Zhenfeng
Z