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Synthesis and olfactory evaluation of allylic α‐quaternary thioether ketones
Author(s) -
Lempenauer Luisa,
Appleson Theresa,
Lemière Gilles,
Duñach Elisabet
Publication year - 2019
Publication title -
flavour and fragrance journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.393
H-Index - 70
eISSN - 1099-1026
pISSN - 0882-5734
DOI - 10.1002/ffj.3477
Subject(s) - thioether , chemistry , allylic rearrangement , patchouli , ketone , sulfur , organic chemistry , alcohol , derivative (finance) , stereochemistry , catalysis , chromatography , essential oil , financial economics , economics
Novel α‐quaternary allylic thioether ketones were efficiently prepared from readily available α,β‐unsaturated ketones in an easily scalable two‐step procedure, with an acid‐catalysed skeletal rearrangement of 2‐(vinylthio) allylic alcohols as the key step. The sensory properties of this novel class of sulfur odorants were evaluated and all displayed green herbal and vegetal notes. An unexpected and interesting fresh patchouli note was observed for an alcohol derivative.