Solvolytic Reactivities of Nortricyclyl, Dehydronorbornyl and Norbornyl Halides. Possible Steric Requirements for Hyperconjugative Resonance¹

Abstract

The present investigation is concerned with the determination and interpretation of the solvolytic reactivities of nortricyclyl (I), endo-dehydronorbornyl (II), exo-dehydronorbornyl (III), endonorbornyl (IV) and exo-norbornyl (V) halides. This series of structurally similar compounds provides an almost unique opportunity to observe the relationship between stereochemistry and solvolytic reactivities in alicyclic halides.