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Effect of solvent on the reactivity of functional groups in polycondensation reactions

1973; Wiley; Volume: 11; Issue: 8 Linguagem: Inglês

10.1002/pol.1973.170110815

1542-9369

Naoya Ogata, Tokuo Ikari,

Synthetic Organic Chemistry Methods

Abstract The effect of solvent on solution or interfacial polycondensations was investigated in terms of selectivity and control of functional groups such as amine or hydroxyl groups toward polycondensation reactions. Solution polycondensation of a mixture of resorcinol (RL) and m ‐xylyenediamine ( m ‐XD) with isophthaloyl chloride was affected by solvents to such extent as to change the course of the polycondensation reaction, and hexamethylenephosphoramide (HMPA) caused the formation of amide‐rich polymer, while tetrahydrofuran (THF) was a solvent favoring formation of a polyamide ester with a regular structure. Polycondensation of 3,3′‐dihydroxybenzidine (DHB) with isophthaloyl chloride yielded exclusively a linear polyamide in HMPA solution, while with aldehyde as a solvent polyester was obtained owing to the preservation of the amine group. Thus, it was found that the course of polycondensation reactions of monomers having different functional groups could be controlled by selection of a suitable solvent.