PREPARATION AND PHOTOLYSIS OF 1-HETEROSUBSTITUTED 1-(1-ALKENYL)BENZOTRIAZOLES

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作者
JOHNSON, AP
DUTTON, JK
PLEYNET, DPM
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O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A Peterson olefination reaction involving 1-trimethylsilanylmethyl-1H-benxotriazole and either adamantanone or acetone, in the presence of n-butyllithium, is used to prepare 1-adamantylidenemethyl-1H-benzotriazole and 1-(2-methylpropenyl)-1H-benzotriazole respectively. Further treatment of these compounds with n-butyllithium and an electrophile affords a variety of 1-heterosubstituted 1-(1-alkenyl)benzotriazoles. Photolysis of the latter compounds yields products from three competing pathways: cyclisation with C-C bond formation, cyclisation with C-S bond formation and halogen atom transfer.
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页码:1913 / 1932
页数:20
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