Tetrahedron

Synthesis of thiacrown and azacrown ethers based on a spiroacetal framework

M Nikac, MA Brimble, RL Crumbie

Index: Nikac, Marica; Brimble, Margaret A.; Crumbie, Robyn L. Tetrahedron, 2007 , vol. 63, # 24 p. 5220 - 5226

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Citation Number: 8

Abstract

A novel class of thiacrown and azacrown ethers incorporating the 1, 7-dioxaspiro [5.5] undecane spiroacetal ring system was prepared by reaction of ditosylate 5 with the appropriate dithiols 9a–c or protected diamine 12a. Spiroacetal ditosylate 5 in turn, was prepared from diol 3 via ozonolysis of bisallyl ether 7 followed by tosylation of the derived diol 8.