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Structure‐Odour Correlation, Part XXIII. 2‐Alkyl‐3a‐methyltetrahydro‐4‐oxa‐l,3‐dithia‐ and −3,4‐dioxa‐1‐thia‐pentalenes
Author(s) -
Weyerstahl Peter,
Hauck Rainer
Publication year - 1996
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/(sici)1099-1026(199607)11:4<203::aid-ffj578>3.0.co;2-g
Subject(s) - chemistry , alkyl , stereochemistry , ring (chemistry) , thiamine , medicinal chemistry , organic chemistry
The 2‐alkyl‐3a‐methyl‐tetrahydro‐4‐oxa‐1,3‐dithiapentalenes 1a‐f were prepared from the chloropentanone 4 , the α‐bromo thioacetates 9a‐f and H 2 S/NEt 3 via the labile intermediates 6a‐f . Likewise, the 3,4‐dioxa‐1‐thia analogues 2a‐f were obtained from 4 and the α‐bromoacetates 10a‐f via 11a‐f . The stereochemistry of the ring fusion and the syn ‐ or anti ‐position of the 2‐alkyl group were assigned by NOED spectra. Flavour evaluation showed that 1b and c possess similar onion‐like, meaty, metallic and sulphury notes as described for the parent compound 1a . The taste of 2a‐f in general exhibits meaty, sulphury, thiamine‐like and fatty tonalities.