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A novel synthesis of cis ‐dihydro‐rose oxide and related stereochemistry
Author(s) -
Liu Chutsin,
Chang Chihsien,
Chou Tsuliang
Publication year - 1984
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570210126
Subject(s) - chemistry , dehydration , diastereomer , rose (mathematics) , catalysis , oxide , stereochemistry , gas chromatography , catalytic hydrogenation , organic chemistry , medicinal chemistry , chromatography , biochemistry , geometry , mathematics
A new synthesis of cis ‐dihydro‐rose oxide from elsholtzia oil is presented. The stereochemistry of catalytic hydrogenation of elsholtziol is discussed, and configurations of the diastereoisomers of the resulting tetrahydroelsholtziol have been deduced with the aid of gas chromatography, infrared spectroscopic analysis and conformational analysis. Stereochemical study of catalytic dehydration of tetrahydroelsholtziols indicates that the dehydration‐rearrangement reactions follow a ( trans ‐elimination process.