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Paper | Regular issue | Vol 27, No. 7, 1988, pp.1629-1636
Published online, 1st January, 1970
DOI: 10.3987/COM-88-4485
Encounter of an Inferior Intramolecular Cyclization in an Approach toward the Synthesis of 10-Oxo-2-thia[3.2]metacyclophane: Preparation of Two Isomeric Dioxo-2,19-dithia[]metacyclophanes

Yee-Hing Lai* and Lay-Hoon Yeo

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


The sodium sulfide coupling of 1,2-bis(3-bromomethhyl)phenylethanone, prepared in seven steps from m,α-dichlorotoluene, was attempted but to yiled the desired 10-oxo-2-thia[3,2]metacyclophane. this is attributed to unfavorable geometry in the thiacyclophane due to introduction of the sp2 carbonyl carbon. Two isomeric dioxo-dithia[3,2,3,2]metacyclophanes were however isolated from the coupling reaction. Both there cyclophanes were found to be conformationally higly mobile by variable-temperature NMR studies.