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Reactions of Alkyl Azidoformates with Norbornylene

1975; NRC Research Press; Volume: 53; Issue: 7 Linguagem: Inglês

10.1139/v75-144

1480-3291

O. E. Edwards, John W. Elder, M. Lesage, Robert W. Retallack,

Photochemistry and Electron Transfer Studies

Evidence is presented that the reactions of alkyl azidoformates with norbornylene induced by direct irradiation do not involve intermediate triazolines. The products of this, and acetophenone-photosenzitized reaction of the mixtures in cyclohexane, are described and contrasted with those from the direct photolysis of the corresponding N-alkoxycarbonyl triazolines. The action of aqueous dioxane at 170° converted 2,3-iminonorbornane (3-azatricylo[3.2.1.0 2,4 ]octane) into 3-aminonortricyclene and syn-7-amino-2-exo-hydroxynorbornane. Three preparations of derivatives of 2-exo-aminonorbornan-3-one are described. The trimethylsilyl ether of the enol of norbornan-2-one (2-trimethylsilyloxynorborn-2-ene) was prepared.