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Synthèses stéréospécifiques et étude organoleptique comparée de onze triméthyl‐2,2,3‐ exo ‐norbornyl‐5‐ exo ‐cyclohexanols racémiques
Author(s) -
Demole Edouard
Publication year - 1969
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19690520730
Subject(s) - chemistry , cyclohexanol , 2 norbornyl cation , stereospecificity , diastereomer , saponification , stereochemistry , organic chemistry , medicinal chemistry , catalysis
The stereospecific syntheses of the eleven racemic 2,2, exo ‐3‐trimethyl‐ exo ‐5‐norbornyl‐cyclohexanols related to the formula VI have been achieved. Moreover, the fragrant properties of these isomeric and stereomeric cyclohexanols have been carefully estimated by a team of four well‐experienced perfumers. In good agreement with our earlier observations [1 ab], it was concluded that the axial 3‐(2,2, exo ‐3‐trimethyl‐ exo ‐5‐norbornyl)‐cyclohexanols, threo (XXIV) and erythro (XXIX), are the only isomers which display a very powerful and genuine sandalwood odour. The other cyclohexanols were found to be about 20–100 times less fragrant (4 compounds), or practically odourless (5 compounds).