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High‐Impact Sulfur Compounds: Constitutional and Configurational Assignment of Sulfur‐Containing Heterocycles

Authors :
Michael Backes
Berthold Weber
Stefan Brennecke
Christoph Krafft
Jakob Ley
Gerhard Krammer
Jörg Grunenberg
Reiner Salzer
Frank Ott
Source :
Chemistry & Biodiversity. 5:1204-1212
Publication Year :
2008
Publisher :
Wiley, 2008.

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.

Details

ISSN :
16121880 and 16121872
Volume :
5
Database :
OpenAIRE
Journal :
Chemistry & Biodiversity
Accession number :
edsair.doi.dedup.....8c8b01be3b8e5fb5da5e3fea1e1a0e99
Full Text :
https://doi.org/10.1002/cbdv.200890097