Bulletin of the Chemical Society of Japan p. 729 - 737 (2000)
Update date:2022-08-03
Topics:
Ishii, Akihiko
Omata, Takenori
Umezawa, Kazuyo
Nakayama, Juzo
2,2,4,4-Tetramethyl-1-phenyl-6,7-dithiabicyclo[3.1.1]heptane was treated with 2KHSO5·KHSO4·K2SO4 to yield cis- and trans-3,6-bis(1,1,3,3- tetramethyl-4-oxo-4-phenylbutyl)-1,2,4,5-tetrathianes. The formation mechanism of the tetrathianes is discussed. X-Ray crystallography disclosed that the cis- and trans-isomers take twist and chair conformations, respectively, in the solid state. Variable-temperature 1H NMR spectroscopy in solution showed that the cis-isomer takes a twist conformation exclusively in the temperature range, whereas the trans-isomer exists as an equilibrium mixture of chair and twist conformers. The cis-tetrathiane reacted with Lawesson's reagent at 50 Γ to give the corresponding di-2-thianyl disulfide.
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(1950)