ChemInform Abstract: Formation, Structure, and Thionation of 1,2,4,5-Tetrathianes [cis- and trans-3,6-Bis (1,1,3,3-tetramethyl-4-oxo-4-phenylbutyl)-1,2,4,5-tetrathianes]

Autor:	Kazuyo Umezawa, Takenori Omata, Juzo Nakayama, Akihiko Ishii
Rok vydání:	2010
Předmět:	Heptane chemistry.chemical_compound chemistry Stereochemistry Reagent Yield (chemistry) Solid-state General Medicine Atmospheric temperature range Twist Medicinal chemistry Conformational isomerism Cis–trans isomerism
Zdroj:	ChemInform. 31
ISSN:	1522-2667 0931-7597
DOI:	10.1002/chin.200027165
Popis:	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 °C to give the corresponding di-2-thianyl disulfide.
Databáze:	OpenAIRE
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