Structural effects in solvolytic reactions. 27. Solvolysis of the exo- and endo-1,2-diphenyl-2-norbornyl and -1,2-dimethyl-2-norbornyl p-nitrobenzoates and chlorides. Evidence for the classical nature of 1,2-disubstituted tertiary 2-norbonyl cations and structure of the parent 2-norbornyl cation

Selective Antibody-Catalyzed Solvolysis of endo-2-Norbornyl Mesylate

“…The norborneol product is exclusively exo since reaction occurs from the direction opposite of that of the bridging interaction. The rate-determining step for the solvolysis reaction involves the formation of transition state 2 elicited to an analogue of this transition state might be expected to sufficiently stabilize the initially formed localized cation 3 relative to the nonclassical ion 4 or slow the conversion of the former to the latter, such that reaction predominantly occurs from the classical cation 3 .…”