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Communication | Regular issue | Vol 78, No. 9, 2009, pp.2201-2208
Published online, 21st May, 2009
DOI: 10.3987/COM-09-11728
Transformation of Hydroxycycloalkanones to Oxabicycloalkenes

Guido Krämer, Heiner Detert, and Herbert Meier*

*Institute of Organic Chemistry, Johannes Gutenberg-University, Duesbergweg 10-14, D-55128, Mainz, Germany

Abstract

Oxabicycloalkenes, which represent anti-Bredt enol ethers, can be generated by catalytic dehydration of the hemiacetals of hydroxycycloalkanones (Method I). Another option is provided by the transformation of hydroxycycloalkanones to the corresponding 1,2,3-selenadiazoles and their thermal fragmentation on Cu powder (Method II). The intermediate hydroxycycloalkynes show a transannular addition of the OH group to the triple bond. Altogether seven new oxabicycloalk-1-enes were obtained by this methods.