title: High-impact sulfur compounds: constitutional and configurational assignment of sulfur-containing heterocycles.
abstract: To unambiguously identify their structures and to evaluate their organoleptic properties, several constitutional und configurational isomers of dialkyl-tetrathianes and dialkyl-pentathiepanes were synthesized by two different synthetic protocols, and separated by preparative gas chromatography. Raman and NMR spectroscopy were used to differentiate between the constitutional 3,6-dialkyl-1,2,4,5-tetrathiane and the 4,6-dialkyl-1,2,3,5-tetrathiane isomers. Furthermore, cis- and trans-isomers of 3,6-dialkyl-1,2,4,5-tetrathianes were distinguished by temperature-dependent NMR experiments. Static, quantum-chemical simulations of the NMR spectra for these cis- and trans-isomers were calculated in the gas layer in order to confirm our experimental assignments. In addition, the assignment of 4,7-alkyl-1,2,3,5,6-pentathiepanes were deducted from their Raman spectra. Dialkyl-tetrathianes and dialkyl-pentathiepanes are interesting components to be used in flavor applications due to their unique olfactory impact and facets.
authors.affiliation: Institute for Analytical Chemistry, Dresden University of Technology, D-01062 Dresden.
authors.forename: Christoph
authors.initials: C
authors.lastname: Krafft
authors.forename: Stefan
authors.initials: S
authors.lastname: Brennecke
authors.forename: Frank
authors.initials: F
authors.lastname: Ott
authors.forename: Michael
authors.initials: M
authors.lastname: Backes
authors.forename: Reiner
authors.initials: R
authors.lastname: Salzer
authors.forename: Jörg
authors.initials: J
authors.lastname: Grunenberg
authors.forename: Jakob P
authors.initials: JP
authors.lastname: Ley
authors.forename: Gerhard E
authors.initials: GE
authors.lastname: Krammer
authors.forename: Berthold
authors.initials: B
authors.lastname: Weber
mesh_terms: D005503:Food Additives / Q000138:chemical synthesis / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013059:Spectrum Analysis, Raman; D013237:Stereoisomerism; D013457:Sulfur Compounds / Q000138:chemical synthesis / Q000737:chemistry; D013649:Taste / Q000187:drug effects
chemical_list: D005503:Food Additives; D006571:Heterocyclic Compounds; D013457:Sulfur Compounds