Reaction of trimethylsilyl azide with bridged bicyclic olefins |
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| Authors: | William R. Peterson Barry Arkles Stephen S. Washburne |
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| Affiliation: | Department of Chemistry, Temple University, Philadelphia, PA 19122 U.S.A.;Petrarch Systems, Levittown, PA 19059 U.S.A. |
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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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| Keywords: | To whom correspondence should be addressed |
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