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High‐Impact Sulfur Compounds: Constitutional and Configurational Assignment of Sulfur‐Containing Heterocycles
Author(s) -
Krafft Christoph,
Brennecke Stefan,
Ott Frank,
Backes Michael,
Salzer Reiner,
Grunenberg Jörg,
Ley Jakob P.,
Krammer Gerhard E.,
Weber Berthold
Publication year - 2008
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.200890097
Subject(s) - chemistry , structural isomer , sulfur , alkyl , raman spectroscopy , conformational isomerism , cis–trans isomerism , computational chemistry , nuclear magnetic resonance spectroscopy , nmr spectra database , organic chemistry , spectral line , molecule , physics , astronomy , optics
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.