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Review | Regular issue | Vol 16, No. 10, 1981, pp.1739-1754
Published online, 1st January, 1970
DOI: 10.3987/R-1981-10-1739
■ The Conformational Behavior in Thia- and Dithiametacyclophanes

Yee-Hing Lai*

*Department of Chemistry, University of Victoria, Victoria, BC V8W 3V6, Canada

Abstract

Thia- and dithiametacyclophanes have been shown to undergo several types of interesting conformational behavior. The coalescence temperature method has been widely used to estimate the various conformational energy barriers. Dithia[n]metacyclophanes exhibit a unique flipping process, the barrier of which largely depends on the substituent at the [n+6]-position. An inversion process is common among thia- and dithia[m.n]metacyclophanes (m = n or m ≠ n). However, substituent(s) at the 9- and/or 18-position(s) of dithia[3.3]metacyclophanes results in variability of the conformer preferred. Most medium-sized dithiametacyclophanes seem to be conformationally very mobile but three dithia[3.1.3.1]metacyclophanes are known to demonstrate a novel “twist-inversion” fluxional behavior.