Synthesis of two novel [2.2]metacyclophanes, 4,6,12,14-tetramethyl and 4,6,12,14-tetramethoxy-1,2,9,10-tetrathia[2.2]metacyclophane

Abstract

The syntheses of two novel 1,2,9,10-tetrathia[2.2]metacyclophanes are described, and the ¹H n.m.r. and mass spectra of the compounds obtained are discussed. These dimers display high stability to electron impact. The ¹H n.m.r. spectra show that the intra-annular aryl protons resonate at dramatically lower field with respect to the corresponding protons in [2.2]metacyclophane (Δδca. 3.6 p.p.m.). Evidence of the ability of the tetramethoxyderivative to generate clathrates trapping volatile organic solvents is also reported.