SYNTHESIS OF CYCLIC ETHERS FROM 1,5CYCLOOCTADIENE.
NAVAL ORDNANCE LAB WHITE OAK MD
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The diformate of 1,5-dihydroxy-2,6-cyclooctyl oxide was synthesized from 1,5-cyclooctadiene. The dihydroxy compound itself was prepared from the diformate by alkaline hydrolysis and a diacetate derivative of the dihydroxy compound has been synthesized by standard methods. While the diformate and diacetate compounds are of general interest as intermediates for the synthesis of systems containing a cyclic ether structure, the dihydroxy compound is of particular interest as a monomer for the synthesis of unique polyester type polymers. A mechanism which involves a transannular reaction is postulated for the formation of cyclic ethers from the diene and this mechanism is compared to the standard olefin hydroxylation mechanism with respect to the products one would expect from each reaction sequence. The proof of structure of the compounds synthesized were determined by elemental and infrared analysis. Author