Syntheses of cyclophanes by photochemical extrusion of sulphur

Multibridged Cyclophanes

“…24 Here, a dithia [3.3]paracyclophane (30) was prepared by coupling of the dibromide 28 with the bisthiol 29 but, rather than oxidizing 30 to the bissulfone, the sulfur was removed by irradiation in trimethyl phosphite. 25 As expected, 1526 chloromethylation with chloromethyl methyl ether-aluminum chloride led to the pseudo-geminal substitution product 32, which is readily cyclized to 22.…”

Medium-sized cyclophanes. Part 18. 5-tert-Butyl-8-substituted [2.2]metaparacyclophanes: preparation, X-Ray diffraction studies, and their treatment with Lewis acids in benzene

“…2 H, s),6.70 (2 H, s) and 6.96(2 H, s); m / z 306 (M+) (Found: C, 89.9; H, 9.9. C23H30 requires C, 90.13; H, 9.87%).…”

An Efficient Route to Symmetrical and Unsymmetrical Disulfide, Thioether, and Hydrocarbon Cyclophanes

“…Taking a different approach, we found reports by Bruhin and Jenny [ 18 ] as well as Boekelheide, [ 19 ] in which treating thioethers with triethylphosphite under UV‐light irradiation extruded sulfurs to give the corresponding saturated hydrocarbons in good yield. Success in repeating the literature preparation for 2,2‐paracyclophane using this method encouraged us to attempt a 3‐step approach to our compounds.…”