염화카바모일술페닐과 그 유도체의 합성

N-Methylidene-2,6-diethylaniline (III) was prepared by the reaction of 2,6-diethylaniline (II) with an excess paraformaldehyde. The protons of N=$CH_2$in the compound III exhibited a second order NMR spectrum. The compound III reacted with bifunctional chlorocarbonylsulfenyl chloride(IV) to give N-(chloromethyl)-N-(2,6-diethylphenyl)-carbamoylsulfenyl chloride(V). The reaction of the compound V with various alcohols resulted in the formation of Alkyl N-(chloromethyl)-N-(2,6-diethylphenyl)-carbamoylsulfenate esters(VI${\sim}$XVI) in 71${\sim}$95% yields. The compound VI${\sim}$XVI decomposed gradually, but the thermal rearrangement of S-O bonding to S=O bonding was not found. The nucleophilic attack of an excess alcohol to the compound Ⅴ was made on both divalent sulfur and ${\alpha}$-carbon of N-chloromethyl group. The corresponding substituted products(XVII, XVIII) had considerable stability. N-Methylidene-2,6-diethylaniline (III)은 2,6-diethylaniline (II)과 과량의 paraformaldehyde와의 반응으로 만들었으며, 이 화합물 III에서 N=$CH_2$ 프로톤은 AB 스핀계를 나타냈다. 화합물 III과 chlorocarbonylsulfenyl chloride(IV)를 반응시켜서 N-(chloromethyl)-N-(2,6-diethylphenyl)-carbamoylsulfenyl chloride(V)를 합성하였다. 화합물 V와 여러 종류의 알콜을 반응시켜서 Alkyl N-(chloromethyl)-N-(2,6-diethylphenyl)-carbamoylsulfenate esters(VI ${\sim}$XVI)를 71{\sim}$95%의 수득률로 합성하였다. VI${\sim}$XVI은 서서히 분해되지만 S-O 결합이 S=O결합으로 변하지는 않았다. 과량의 알콜은 V의 2가 황과 N-chloromethyl기의 ${\alpha}$-탄소에 대해 친핵성 공격을 할 수 있었으며, 이렇게 하여 생긴 화합물 (XVII, XVIII)은 상당한 안정성을 가지고 있었다.