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KMID : 1059519990430010074
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Journal of the Korean Chemical Society
1999 Volume.43 No. 1 p.74 ~ p.84
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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
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Kang Yoon-Ho
Kim Kyong-Tae
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Abstract
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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 Bu3SnH 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 Bu3SnH 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)-l-hexenyl phenyl selenides with Bu3SnH in the presence of AIBN gave 6-aryl-6-phenylamino-l-hexene (9-31%) and 1-aryl-1-oxo-5-pentene (15-44%). A mechanism for the formation of the products is proposed.
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