19578-76-8Relevant academic research and scientific papers
Towards ortho-selective electrophilic substitution/addition to phenolates in anhydrous solvents
Lopu?anskaja, Eleana,Kooli, Anni,Paju, Anne,J?rving, Ivar,Lopp, Margus
, (2021/02/16)
Alkyl-substituted Li-phenolates with BnBr in water solution lead to a mixture of o- and p-Bn-substituted phenols together with a substantial amount of phenol Bn ether. In CPME, and especially in toluene with 1–2 equivalents of ether or alcohol additives, ortho-selective alkylation is achieved. In the case of o,o,p-tri- and o,o-di-substituted phenols dearomatization occurs affording o-Bn-substituted alkyl cyclohexadienones with yields up to 92% with an o/p ratio up to 90/1.
Counterattack mode differential acetylative deprotection of phenylmethyl ethers: Applications to solid phase organic reactions
Chakraborti, Asit K.,Chankeshwara, Sunay V.
supporting information; experimental part, p. 1367 - 1370 (2009/07/04)
A counterattack protocol for differential acetylative cleavage of phenylmethyl ether has been developed. The phenylmethyl moiety is liberated as benzyl bromide that is isolated and reused providing advantages in terms of waste minimization/utilization and atom economy. The applicability of this methodology has been extended for solid phase organic reactions with the feasibility of reuse of the solid support.
Electron transfer induced dissociations of 2- and 4-alkyl cyclohexadienones
McCarroll, Andrew J.,Crayston, Joe A.,Walton, John C.
, p. 4275 - 4280 (2007/10/03)
Several 2- and 4-alkylcyclohexadienones were prepared and shown to accept electrons to produce ketyl radical anions that dissociated rapidly at room temperature to release carbon-centered radicals and an aromatic phenoxide type anion. In the PET process with benzyl-substituted cyclohexadienones, initiated with triethylamine, the benzyl radicals dimerised or abstracted an H-atom from solvent. In electrochemical reductions, and in reductions with alkali metals in liquid ammonia, the benzyl radicals were further reduced to anions.
