115152-71-1Relevant articles and documents
Controlled preparation of amphiphilic triblock-copolyether in a metal- and solvent-free approach for tailored structure-directing agents
Balint, Alexander,Papendick, Marius,Clauss, Manuel,Müller, Carsten,Giesselmann, Frank,Naumann, Stefan
, p. 2220 - 2223 (2018)
Under mild conditions, PPO-PEO-PPO ("reverse Pluronics") and PBO-PEO-PBO copolyether were generated by way of N-heterocyclic olefin-based organocatalysis. Reverse Pluronics with molar masses > 20 000 g mol-1 could be synthesized with excellent control (DM ≤ 1.03) and were converted into (ordered) mesoporous carbons via organic self-assembly to showcase the need for tailor-made copolymer as structure-directing agent.
N-Heterocyclic Olefins as Organocatalysts for Polymerization: Preparation of Well-Defined Poly(propylene oxide)
Naumann, Stefan,Thomas, Anthony W.,Dove, Andrew P.
, p. 9550 - 9554 (2015)
The metal-free polymerization of propylene oxide (PO) using a special class of alkene - N-heterocyclic olefins (NHOs) - as catalysts is described. Manipulation of the chemical structure of the NHO organocatalyst allows for the preparation of the poly(propylene oxide) in high yields with high turnover (TON>2000), which renders this the most active metal-free system for the polymerization of PO reported to date. The resulting polyether displays predictable end groups, molar mass, and a low dispersity (D strok signM1.09). NHOs with an unsaturated backbone are essential for polymerization to occur, while substitution at the exocyclic carbon atom has an impact on the reaction pathway and ensures the suppression of side reactions. One carbon makes a difference: The efficient and controlled formation of poly(propylene oxide) (PPO) at a very low catalyst loading of N-heterocyclic olefins showcases the use of this group of highly polarized alkenes as catalysts for organopolymerization. A strong structure-activity relationship is found, which is fundamentally different from the reactivity of N-heterocyclic carbenes (TON=turnover number, PDI=polydispersity index).
Unexpected oxidative C-C cleavage in the metallation of 2-substituted imidazolium salts to give N-heterocyclic carbene complexes
Chianese, Anthony R.,Zeglis, Brian M.,Crabtree, Robert H.
, p. 2176 - 2177 (2007/10/03)
Imidazolium salts blocked at C2 with methyl or benzyl groups unexpectedly react with silver oxide to give N-heterocyclic carbene complexes of silver via an oxidative carbon-carbon bond cleavage.