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

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 com...

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Bibliographic Details
Published inHeterocycles Vol. 37; no. 3; pp. 1913 - 1932
Main Authors JOHNSON, AP, DUTTON, JK, PLEYNET, DPM
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 05.05.1994
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CHEMISTRY
N-SUBSTITUTED BENZOTRIAZOLES
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Summary: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.
ISSN:0385-5414