
%0 Journal Article
%A Coxon, JM 
%A Hartshorn, MP 
%A Swallow, WH 
%T A study of hydroxyl participation in acyclic epoxide systems. Acid-catalysed rearrangements of <I>trans</I>- and <I>cis</I>-3,4-Epoxypentan-1-ols, 4,5-Epoxyhexan-1-ols, and 5,6-Epoxyheptan-1-ols
%J Australian Journal of Chemistry
%D 1973/11/01
%V 26
%N 11
%P 2521-2526
%K 
%R https://doi.org/10.1071/CH9732521
%U https://www.publish.csiro.au/paper/CH9732521 
%X The acid-catalysed rearrangements of trans- and cis-4,5-epoxyhexan-1- ols and 5,6-epoxyheptan-1-ols demonstrate a preference for cyclic ether formation: tetrahydrofuran > tetrahydropyran > oxepan. The ether products arise by intramolecular hydroxyl displacement of the epoxide oxygen with inversion of configuration. Reactions of trans- and cis- epoxypentan-1-ols give a mixture of trans- and cis-2-methyl-tetrahydro- furan-3-ols (8) and (9). From each epoxide one methyltetrahydrofuranol must arise by nucleophilic displacement of the secondary epoxide oxygen with retention of configuration. 
