27397-04-2Relevant academic research and scientific papers
Structural and Mechanistic Effects on the Rates of Ring-Opening Reactions in the 5-16-Membered-Ring Region
Cerichelli, Giorgio,Illuminati, Gabriello,Lillocci, Claudio
, p. 3952 - 3957 (2007/10/02)
Partial rate coefficients have been determined for the reaction of cyclic dimethylammonium ions with sodium methoxide in the 7-16-membered-ring region.Three second-order parallel reactions take place and lead to exocyclic demethylation (A), ring-opening substitution (B), and ring-opening olefin-forming elimination (C).The results were compared with the behavior of the five- and six-membered rings.Reaction A shows negligible dependence on ring size.In contrast, reactions B and C are affected by ring size through ring strain and geometry of the transition state: the latter factor is held responsible for major differences in the reactivity profiles between such reactions.
