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Reaction of Trimethylsilyl Azide with Bridged Bicyclic Olefins by William R. Peterson Jr.; Barry Arkles; Stephen S. Washburne is a Chemistry article available to read on EtoBox.

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Bridged bicyclic olefins were found to undergo facile 1,3-cycloaddition reaction with trimethylsilyl azide. Norbornene produced cis,exo-l-trimethylsilyl-4,7-methano-3a.4,5,6,7,7a-hexahydrole, while norbornadiene formed a diadduct with cis,exo-stereochemistry, together with 2-trimethylsilyl-1,2,3-triazole produced by a retro-DieleAlder reaction of an intermediate mono-adduct. Dicyclopentadiene reacted only at the norbornene position while ar-pinene did not react with trimethylsilyl azide. In contrast to aryl-and sulfonyl-azide adducts of norbornene derivatives, which decompose upon heating, the present adducts were recovered unchanged after prolonged treatment at 205°C. the corresponding a+ridine: 1 .: -H-.H, -. '. 7 . . All the.trimethylsilyltriazolines isolated (Ia, Ib, II and IV) exhibited surprising thermal stability\_ In contrast with a$-and sulfonyl-azide adducts of bi-

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Author

William R. Peterson Jr.; Barry Arkles; Stephen S. Washburne

Publisher

Elsevier Science; Elsevier ; Elsevier BV (ISSN 0022-328X)

Published

1976

Language

EN

Field

Chemistry (Physical Sciences)