Aminolysis and Polymerization of 3‐(p‐Toluenesulfonoxy)Hydantoin

Abstract

Aminolysis of 3‐(p‐toluenesulfonoxy)hydantoin (I) through two alternative routes led to the formation of series of both methylene‐diurea derivatives(II) and ω‐arylsemicarbazido (N‐arylacetamides) (III). 3‐(p‐Toluenesulfonoxy)hydantoin was found to undergo a novel kind of polymerization reaction induced by triethylamine, yielding a new polymer structure which consists of hydantoin groups combined by a hydrazinic linkage. 5‐Isopropyl‐3‐(p‐toluenesulfonoxy) hydantoin (IV) was prepared here from α‐isopropylmalonic acid diethyl ester, via α‐isopropylmalonohydroxamic acid (V); properties of this compound were also studied.