Tetrahedron

Unusual cyclodimerization of small cyclic ethers via neighboring carbonyl-group participation and cation transfer

S Kanoh, T Nishimura, M Naka, M Motoi

Index: Kanoh, Shigeyoshi; Nishimura, Tomonari; Naka, Masashi; Motoi, Masatoshi Tetrahedron, 2002 , vol. 58, # 35 p. 7065 - 7074

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Citation Number: 9

Abstract

Oxetanes having both a carbonyl functional group and a phenyl group at the 3-position bring about unusual cyclodimerization under the influence of trifluoromethanesulfonic acid, to give a cis/trans-isomer mixture of substituted 1, 3-dioxanes via neighboring carbonyl-group participation, cation transfer including phenonium rearrangement, and cyclodimerization. Oxiranes having a carbonyl functional group also undergo a similar cyclodimerization to ...