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Abstract
Bridged bicyclic olefins were found to undergo facile 1,3-cycloaddition reaction with trimethylsilyl azide. Norbornene produced cis,exo-1-trimethylsilyl-4,7-methano-3a,4,5,6,7,7a-hexahydrobenzotriazole, while norbornadiene formed a diadduct with cis,exo-stereochemistry, together with 2-trimethylsilyl-1,2,3-triazole produced by a retro-Diels—Alder reaction of an intermediate mono-adduct. Dicyclopentadiene reacted only at the norbornene position while α-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.
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