The Journal of Organic Chemistry

Synthesis of [3.3] heterophanes containing the pyridine, furan, and thiophene rings by the TosMIC method

T Shinmyozu, Y Hirai, T Inazu

Index: Shinmyozu, Teruo; Hirai, Yoshio; Inazu, Takahiko Journal of Organic Chemistry, 1986 , vol. 51, # 9 p. 1551 - 1555

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Citation Number: 43

Abstract

3.3](2, 5)-and [3.3](2, 6) pyridinophanes as well as [3] metacyclo [3](2, 5) furanophane (20) and [3] metacyclo-[3](2, 5) thiophenophane (23) have been synthesized by the conventional or modified TosMIC coupling reaction, followed by acid treatment and reduction. lH NMR data suggest that the stable conformation of the [3.3]-metacyclophane-2, ll-dione system (3, 6, 19, and 22) is anti, whereas that of the [3.3] metscyclophane system (4, 7, 20, and 23) is ...