30649-19-5Relevant articles and documents
Pd-catalyzed C=C double-bond formation by coupling of N-tosylhydrazones with benzyl halides
Xiao, Qing,Ma, Jian,Yang, Yang,Zhang, Yan,Wang, Jianbo
scheme or table, p. 4732 - 4735 (2009/12/24)
Pd-catalyzed reaction of N-tosylhydrazones with benzyl halides affords di- and trisubstituted olefins In high yields with excellent stereoselectivity. This coupling reaction Is supposed to proceed through a migratory insertion of Pd carbene species.
Polylithiumorganic compounds -19. Regioselective carbon-carbon σ-bond scission followed by a 1,6-proton shift upon the reductive metalation of benzylidenecyclopropane derivatives with lithium metal
Maercker, Adalbert,Daub, Volker E. E.
, p. 2439 - 2458 (2007/10/02)
Depending on the substituent α-substituted benzylidenecyclopropanes (32) react more or less readily with lithium dust (2% sodium) in diethyl ether whereby a regioselective scission of only the cyclopropane σ-bond cis to the phenyl ring takes place. Upon raising the temperature the primarily formed 1,3-dilithiumorganic compound due to an agostic interaction rearranges by a 1,6-proton shift into a doubly bridged 1,4-dilithio compound. With α-methylbenzylidenecyclopropane (32c) this rearrangement was shown to occur intermolecularly via a trilithiumorganic compound 56. The suggested mechanism of these reductive metalation reactions via a bisected radical anion 87 where the lithium is mainly bound to the cyclopropyl carbon atom and oriented syn to the phenyl ring, was supported by MNDO (geometries) and ab initio (energies) calculations.
