107378-68-7Relevant articles and documents
Influence of the reaction temperature on some acid-catalized processes of 6-hydroxy-4-oxa-alkanal derivatives and related products. Ring contraction in 5-alkoxy-1,4-dioxepanes
Espinosa, Antonio,Gallo, A. Miguel,Campos, Joaquin,Entrena, Antonio
, p. 379 - 383 (2007/10/02)
The qualitative effect of the reaction temperature on some acid-catalized processes carried out on 6-hydroxy-4-oxa-alkanal derivatives may be rationalized by means of two simultaneous or competitive pathways which involve intermediates such as 5-alkoxy-1,4-dioxepane derivatives or vinyl dioxolanes.We describe herein an acid catalyzed contraction of the 5-isopropoxy-1,4-dioxepane ring in dioxane and different alcohol interchange reactions with 5-alkoxy-1,4-dioxepanes that also occur with ring contraction when the reaction temperature is 60 deg C or higher.The transacetalization reactions between 6-hydroxy-4-oxa-hexal ethylene acetal and 6-hydroxy-4-oxa-heptanal 1,2-propylene acetal and tert-butanol, carried out at the reflux of the reacting mixtures are also described.The results obtained suggest 2-vinyl-1,3-dioxolanes as reactive intermediates.In order to prove this hypothesis the reaction between 2-vinyl-1,3-dioxolane and tert-butanol at reflux has been stuied.It leads to the same reaction products.
