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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 40, Number 9
JKCSEZ 40(9)
June 20, 1996 

Synthesis of 1-(Benzotriazol-1-yl)alkyl Aryl Sulfones

1-(Benzotriazol-1-yl)alkyl Aryl Sulfone의 합성
Young-Seuk Hong, Hyun-Muk Kim, Jeong-Geun Lee, Yong-Tae Park, Ho-Sik Kim

1-(Benzotriazol-1-yl)-1-benzenesulfonylmethane 1a에 LDA 및 methyl iodide를 작용시켜 1-(benzotriazol-1-yl)-1-benzenesulfonylethane 2a와 1-(benzotriazol-1-yl)-1-benzenesulfonylpropane 2b를 각각 얻었다. 같은 방법으로 1-(benzotriazol-1-yl)-1-toluenesulfonylmethane 1b로부터 1-(benzotriazol-1-yl)-1-toluenesulfonylpropane 3a와 1-(benzotriazol-1-yl)-1-toluenesulfonylpentane 3b를 얻었다. 한편, 1,1-di(benzotriazol-1-yl)-1-arylmethane 4를 butyl lithium과 diphenyl disulfide로 처리하여 1,1-di(benzotriazol-1-yl)-1-aryl-1-thiophenoxymethane 9a와 1,1-di(benzotriazol-1-yl)-1,1-dithiophenoxymethane 9b를 각각 얻었다. 화합물 9a를 m-CPBA로 산화시켜 1,1-di(benzotriazol-1-yl)-1-benzenesulfoxymethane 10a와 1,1-di(benzotriazol-1-yl)-1-benzenesulfonylmethane 10b을 얻었다. 한편, 화합물 3b를 170℃에서 열분해시켜 3-toluenesulfonyl-2-pentene 11을 얻었으며, 150℃의 강철봄베속에서 3b를 과량의 물로 가수분해시켰더니 sulfone의 C-N 및 C-S 결합 모두가 절단된 diethyl ketone 13a가 생성됨을 확인하였다.

(Benzotriazol-1-yl)arenesulfonylalkanes, 2a, 2b, 3a and 3b, were prepared by lithiation of 1-(benzotriazol-1-yl)arenesulfonylmethanes followed by reaction with alkyl iodides. Very bulky molecules such as 1,1-di(benzotriazol-1-yl)-1-aryl-1-thiophenoxymethanes 5, 1,1-di(benzotriazol-1-yl)-1-thiophenoxymethane 9a and 1,1-di(benzotriazol-1-yl)-1,1-dithiophenoxymethane 9b were synthesized. 1,1-Di(benzotriazol-1-yl)-1-benzenesulfoxymethane 10a and 1,1-di(benzotriazol-1-yl)-1-benzenesulfonylmethane 10b were also synthesized by the oxidation of compound 9a, while oxidation of sulfide group on compound 5 and 9b by m-CPBA were not successful. On the other hand, pyrolysis and hydrolysis of 3-(benzotriazol-1-yl)-3-toluenesulfonylpentane 3b gave 3-toluenesulfonyl-2-pentene 11 and diethyl ketone 13a, respectively, which means there are both C-N and C-S bond cleavages.

615 - 622
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