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Report | Regular issue | Vol 23, No. 5, 1985, pp.1205-1214
Published online, 1st January, 1970
DOI: 10.3987/R-1985-05-1205
Isolation of 2,18-Dithia[]metacyclophane and 2,3,19,20-Tetrathia[]metacyclophane from Coupling Reactions Directed toward the Synthesis of Strained Thiacyclophanes

Yee-Hing Lai* and Teong-Beng Soo

*Department of Pharmacy, National University of Singapore, Lower Kent Ridge Road, 119260, Singapore


Intramolecular coupling reactions of bis(3-bromomethylphenyl)methane or bis(3-mercaptomethylphenyl)methane failed to yield the strained thia[3.1]- and dithia[4.1]metacyclophanes respectively. Two previously unknown medium-sized cyclophanes, namely a dithia[]metacyclophane and a tetrathia[]metacyclophane, have been isolated and characterized. Variable temperature NMR studies have revealed that both these metacyclophanes have a very high degree of conformational mobility.