New Click Chemistry: Click Polymerization via 1,3-Dipolar Addition of Homo-ditopic Aromatic Nitrile Oxides Formed In Situ

Abstract

New click chemistry is demonstrated. Click polymerization proceeded via 1,3-dipolar polycycloaddition of homo-ditopic nitrile oxides to bifunctional terminal olefinic and acetylenic monomers as dipolarophiles. Molecular sieves (MS 4A) served as an efficient promoter for the polymerization to afford polyisoxazolines and polyisoxazoles in high yields.

Synthesis of 3,5-Disubstituted Isoxazoles and Isoxazolines in Deep Eutectic Solvents

“…This green approach has been conducted by different oxidative reagents such as oxone, [43][44] iodine, [45][46][47] iodobenzene trifluoroacetate, 48 iodobenzene diacetate, [49][50][51] tert-butyl hypoiodite 52 or chloramine-T. 53 However, these new protocols have several inconveniencies such as stability, price and manipulation of reagents. The importance of the used solvent has been recently addressed by the use of aqueous biphasic protocols, [54][55] ionic liquid, 56 and aqueous polyethylene glycol. 57 Within the framework of green chemistry, solvents occupy a strategic place.…”

Fluorescent poly(boron enaminoketonate)s: synthesis via the direct modification of polyisoxazoles obtained from the click polymerization of a homoditopic nitrile N-oxide and diynes

“…Building upon our previous study, [24][25][26][27][28][29][30][31][32][33][34][35][36] we selected bis(2-alcoxy-naphthalene nitrile N-oxide) as a skeleton, speculating that it should serve well as a framework for a sufficiently-stabilized homoditopic nitrile N-oxide. Synthesis of the homoditopic nitrile N-oxide 1 was accomplished in 58% overall yield via a three-step reaction (Scheme 1, m.p.…”

Ultra Rapid Approaches to Mild Macromolecular Conjugation

“…Furthermore, such chemistry has also been effectively employed as a mechanism for step-growth polymerization, however not under ambient conditions. [78,79] It is also worth noting that the isoxazole that is formed after such a cycloaddition may be partially reduced to baminoenone groups or fully reduced to b-aminoalcohol groups. Such generation of new functional groups (with relative ease) has already been proven to be successful in the formation of crosslinked polymer networks.…”