Novel Ring-Expansion Reaction between Formaldehyde Cyclic Acetal and Ethylene Oxide

摘要

We formerly found the novel ring-expansion reaction between 1, 3, 5-trioxane and ethylene oxide, and identified threee novel compounds. Now, we found this type of reaction can be generalized to the ring-expansion reaction between formaldehyde cyclic acetal and ethylene oxide. We, first, confirmed this type of reaction between 1, 3-dioxolane and ethylene oxide to form 1, 3, 6-trioxacyclooctane, 1, 3, 6, 9-tetraoxacycloundecane and 1, 3, 6, 9, 12-pentaoxacyclotetradecane. When the initial ethylene oxide concentration is low, the formation of 1, 3, 6-trioxacyclooctane is predominant and selectivity for the formation of 1, 3, 6-trioxacyclooctane is nearly 99%. However, with the increase in initial ethylene oxide concentration, the formation of mixed reaction products of 1, 3, 6-trioxacyclooctane, 1, 3, 6, 9-tetraoxacycloundecane and 1, 3, 6, 9, 12-pentaoxacyclotetradecane was observed. Further we confirmed the similar type of ring-expansion reaction between 1, 3-dioxacycloheptane and ethylene oxide. From these observations, we concluded the general ring-expansion reaction between formaldehyde cyclic acetal and ethylelne oxide is valid.