A Reinvestigation of the Preparation, Properties, and Applications of Aminomethyl and 4-Methylbenzhydrylamine Polystyrene Resins¹

Abstract

Mild, efficient conditions have been developed for the preparation of 4-methylbenzhydrylamine polystyrene (MBHA) and aminomethyl polystyrene (AMPS) resins by a two-step procedure with synthons 1a and 1c. The products possess excellent swelling characteristics and acylate readily with linkers yielding useful derivatives, which retain good swelling and reactivity. Comparative studies with these resins, and their poly(ethylene glycol) (PEG) derivatives, yield insights into the role of spacer arm and environment effects in synthesis facilitation.

Polymer‐Supported Chiral Organocatalysts: Synthetic Strategies for the Road Towards Affordable Polymeric Immobilization

“…Towards the end of the 1990s, two further important resins of the same type were developed, [12][13] Champion I and II (5 and 6, NovaGel) [12] and ArgoGel (7). [13] The first of these is prepared through a rather lengthy synthesis where a standard PS resin is aminoalkylated and then coupled to hetereobifunctional PEG derivatives, usually followed by further modifications.…”

“…[13] The first of these is prepared through a rather lengthy synthesis where a standard PS resin is aminoalkylated and then coupled to hetereobifunctional PEG derivatives, usually followed by further modifications. [12] The ArgoGel family are important commercial products that are prepared by treating the Merrifield resin with methylmalonic ethyl ester in a nucleophilic substitution to give an immobilized branching point diester that is subsequently reduced to a diol, whereupon ethylene oxide is grafted by anionic polymerization. [13] In the same period, a quite elegant way of introducing a nonbenzylic alcohol directly onto non-derivatized and crosslinked PS using propylene oxide and Lewis acid was reported.…”

A síntese orgânica em fase sólida e seus suportes poliméricos mais empregados

“…No exemplo citado, uma das estratégias escolhidas para contornar esta limitação é a modificação de resinas constituídas de polietilenoglicol 29 , aproveitando as características físicas desse álcool. Concomitante ao desenvolvimento de novos arcabouços, há a procura por novos ligantes, visando a obtenção de uma maior diversidade química nas resinas empregadas 55,56 . De fato, os trabalhos publicados atualmente propõem uma imensa gama de grupos funcionais disponíveis para reagir com os mais variados tipos de substratos.…”

1,6‐hexanediol diacrylate‐crosslinked polystyrene: Preparation, characterization, and application in peptide synthesis

“…The developments of poly(ethylene glycol) (PEG)-grafted PS resin [7][8][9][10] or PS crosslinked with PEG moiety [11][12][13][14][15][16] are some of the approaches to circumvent the problems associated with DVB-based resins. Recently, we have shown the utility of 1,4-butanediol dimethacrylate-crosslinked PS (BDDMA-PS) in solid-phase peptide synthesis (SPPS).…”