92577-91-8Relevant academic research and scientific papers
Aerial dioxygen activation: Vs. thiol-ene click reaction within a system
Choudhuri, Khokan,Mandal, Arkalekha,Mal, Prasenjit
supporting information, p. 3759 - 3762 (2018/04/16)
Markovnikov or anti-Markovnikov selective thiol-ene click (TEC) reactions and the synthesis of β-hydroxysulfides via aerial dioxygen activation are prevalent C-S bond forming reactions of styrenes and thiophenols. Herein, by choosing appropriate environme
Nucleophilic addition to iminium ethers in the preparation of functionalized N-alkyl heterocycles
Fenster, Erik,Smith, Brenton T.,Gracias, Vijaya,Milligan, Gregory L.,Aube, Jeffrey
, p. 201 - 205 (2008/09/16)
(Chemical Equation Presented) Bicyclic iminium ethers can be synthesized by the reactions of ketones with hydroxyalkyl azides. These cationic species react with a variety of nucleophiles via two possible pathways. The initially formed, kinetic product arises from direct addition to the iminium carbon in the substrate. In some cases, the initial adduct reverts to the starting iminium ether and the ultimate product arises from nucleophilic displacement at the O-alkyl group to afford the terminally functionalized N-substituted amide. The behavior of a range of nucleophiles was studied by using several iminium ethers. In general, the relevant pathway could be identified by characterization of the product formed. For hydroxide addition, which can afford only one product regardless of mechanism, the reaction was shown to arise by the kinetic pathway, using 18O-labeled hydroxide. A one-pot synthesis of functionalized lactams entailing treatment of ketones first with hydroxyalkyl azides followed by nucleophilic addition was also developed.
