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■ A Rigid Conformation for 5-Fluoro-2,11-dithia[3.3](1,4)naphthalenometacyclophane with Absence of Meta-ring Flipping

Yee-Hing Lai and Thian-Guan Peck

*Department of Chemistry, National University of Singapore, 10 Kent Ridgh Crescent, 119260, Singapore

Abstract

¹⁹F and ¹H nmr data suggest the presence of only one major isomer for the title compound with the unexpected stacking of the benzene and naphthalene rings. Variable temperature ¹H nmr studies suggested no meta-ring flipping even at 160°C. The chemical shifts of the methylene protons were observed to be solvent and temperature dependent. This is attributed to the solvent effects on inversion processes of the bridges.