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- W2510477666 abstract "벤조트리아졸을 보조체로 사용하는 유기합성법은 거의 대부분 이온성 반응 메카니즘으로 설명되며 라디칼 반응을 이용한 벤조트리아졸의 응용은 거의 없었다. 벤조트리아졸의 N-1의 ${alpha}$ 위치 탄소 원자에 라디칼 중심을 만든 후 벤조트리아졸의 다섯고리를 형성하는 질소 원자중에서 질소 분자가 빠져나감으로서 생성되는 페닐 라디칼의 반응을 연구하기위해 1[(aryl)(phenylseleno)methyl]benzotriazole, AIBN, 그리고 $Bu_3$ SnH을 벤젠에 용해시키고 환류시켜 주었다. 이 반응 혼합물로 부터 2-aminodiphenyl selenide (16∼29%), 2-aminobiphenyl (9∼15%), diphenyl diselenide (30∼93%), 1-(arylmethyl)benzotriazole (9∼39%), 그리고 tributyltinphenyl selenide (10∼36%)을 얻었으며, AIBN없이 과량의 $Bu_3$ SnH 존재하에 같은 조건하에서 반응시키는 경우,diphenyl diselenide (53∼100%), benzotriazole (27∼35%) 그리고 1-(arylmethyl)-benzotriazole (16∼33%)와 함께 arylmethylidenaniline이 과량의 $Bu_3S_nH$ 에 의해 환원된 N-(arylmethyl)anilines (44∼66%)이 생성되었다. 같은 조건 하에서 6-aryl-6-(benzotriazol-1-yl)-1-hexenyl phenyl selenides, AIBN, 그리고 $Bu_3$ SnH의 반응으로부터 6-aryl-6-phenylamino-1-hexene(9∼31%)과 1-aryl-1-oxo-5-pentene (15∼44%)을 얻었다. 이들 생성물의 생성 메카니즘을 제시하였으며 벤조트리아졸이 합성 보조체로 이용된 경우 $Bu_3$ SnH에 의해 벤조트리아졸의 세개의 질소 원자를 포함하는 다섯원자고리로 부터 라디칼 반응에 의해 질소 분자가 빠져나가는 것을 보여준 새로운 예이다. 【Most of the reactions involving benzotriazoles as a synthetic auxiliary have been explained by ionic mechanisms, whereas benzotriazole-mediated radical reactions have received little attention. The reaction of 1-[(aryl)(phenylseleno)methyl]benzotriazole with $Bu_3$ SnH in the presence of AIBN in benzene at reflux gave 2-aminodiphenyl selenide (16-29%), 2-aminobiphenyl (9-15%), diphenyl diselenide (30-93%), 1-(arylmethyl) benzotriazole (9-39%) and tributyltin-phenyl selenide (10-36%), whereas the compounds were treated with excess molar amount of $Bu_3$ SnH in the absence of AIBN to afford N-(arylmethyl)anilines (44-66%) along with diphenyl diselenide (53-100%), benzotriazole (27-35%) and 1-(arylmethyl)benzotriazole (16-33%). Similarly, treatment of 6-aryl-6-(benzotriazol-1-yl)-1-hexenyl phenyl selenides with $Bu_3$ SnH in the presence of AIBN gave 6-aryl-6-phenylamino-1-hexene (9-31%) and 1-aryl-1-oxo-5-pentene (15-44%). A mechanism for the formation of the products is proposed.】" @default.
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- W2510477666 date "1999-01-01" @default.
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- W2510477666 title "Mechanistic Studies on the Reactions of 1-[(Aryl)(phenylseleno)methyl]benzotriazoles and 6-Aryl-6-(benzotriazol-1-yl)-1-hexenyl Phenyl Selenides with Tributyltin Hydride" @default.
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