G. Frachey et al., RING-OPENING REACTIONS .7. RING-SIZE EFFECTS ON THE REACTIVITIES OF 1,1,2,2,OMEGA,OMEGA-HEXAMETHYL CYCLIC AMMONIUM-IONS IN THE EXOCYCLIC ELIMINATION-REACTION, Gazzetta chimica italiana, 123(8), 1993, pp. 463-466
The reactivities of cyclic ammonium ions (3-, 4-, 5-, and 6-membered r
ings) have been determined in a ring-opening elimination reaction. The
comparison with analogous reactivity data obtained in previous work o
n the ring-opening substitution reaction suggests a substantial differ
ence in the effect of the stereochemical factors governing the two rin
g-opening reactions and confirms the anomalous behaviour of small ring
s in the ring-opening substitution reaction.