Synthesis and conformational properties of [n. 1.1] paracyclo (2, 5) thiophenoparacyclophanes

Y Miyahara, T Inazu, T Yoshino

Index: Miyahara, Yuji; Inazu, Takahiko; Yoshino, Tamotsu Journal of Organic Chemistry, 1984 , vol. 49, # 7 p. 1177 - 1182

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Citation Number: 13

Abstract

Cyclic diketo sulfides 4 (n= 3-8, lO) were condensed with glyoxal to give thiophenophanediones 6. The NMR, IR, and UV spectral data of 6 are consistent with the following picture. The thiophene-2, 5-dicarbonyl moiety in 6 (n= 10) is in the mean molecular plane and, unlike the corresponding open chain compounds, in an O, S, O trans, trans conformation. As n decreases, the benzene rings gradually become face-to-face as ...