Formation of 1,4,7,10-Tetraoxacyclotetradecane by a Novel Ring-Expansion Reaction of 1,3-Dioxacycloheptane with Ethylene Oxide

Naoaki YAMASAKI† and Junzo MASAMOTO*

Fukui University of Technology; Gakuen, 3-6-1 Gakuen, Fukui-shi 910-8505 Japan
First Department of Additives Technology, Asahi Kasei Corporation; 6-2700, Asahi-machi, Nobeoka-shi 882-0847 Japan

We found a novel ring-expansion reaction of 1,3-dioxacycloheptane with ethylene oxide to form 1,4,7,10-tetraoxacyclotetradecane. The reaction is thought to be composed of the following three steps: first, formation of an active intermediate from 3 mol of ethylene oxide and 1 mol of 1,3-dioxacycloheptane; second, elimination of formaldehyde from the intermediate; and finally, cyclization to form 1,4,7,10-tetraoxacyclotetradecane. The relation between the ring size and the ring strain energy is thought to be deeply involved in a significant factor in this novel reaction.

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