title: Synthesis of oleophilic electron-rich phenylhydrazines.
abstract: Phenylhydrazines 1 substituted with two or three long-chain alkyl, alkoxy or alkylsulfanyl groups were successfully prepared by acid-induced removal of the Boc group in hydrazides 2. The reaction is carried out with 5 equivalents of TfOH in CF(3)CH(2)OH/CH(2)Cl(2) at -40 °C for 1.5 min. Under these conditions, the deprotected hydrazine 1 is fully protonated, which increases its stability in the reaction medium. The hydrazines were isolated in 60-86% yields and purities >90%. The hydrazides 2 were obtained in 43-71% yields from aryl bromides 5, which were lithiated with t-BuLi and subsequently reacted with di-tert-butyl azodicarboxylate (DTBAD).
authors.affiliation: Organic Materials Research Group, Department of Chemistry, Vanderbilt University, Nashville, TN 37235.
authors.forename: Aleksandra
authors.initials: A
authors.lastname: Jankowiak
authors.forename: Piotr
authors.initials: P
authors.lastname: Kaszyński