
TY  - JOUR
A1  - Coxon, JM 
A1  - Hartshorn, MP 
A1  - Swallow, WH 
T1  - 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
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1973
VL  - 26
IS  - 11
SP  - 2521
EP  - 2526
KW  - 
UR  - https://doi.org/10.1071/CH9732521 
N2  - 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. 
ER  -

