Kadival, M. V. ; Nair, M. S. R. ; Bhattacharyya, S. C. (1967) Terpenoids-XCVI: dehydraton reaction of guaiol and dihydroguaiols and transformation of 1α,5α-dihydroguaiol to 1α,5α-hexahydrodehydrocostus lactone Tetrahedron, 23 (3). pp. 1241-1249. ISSN 0040-4020
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Official URL: http://linkinghub.elsevier.com/retrieve/pii/004040...
Related URL: http://dx.doi.org/10.1016/0040-4020(67)85074-9
Abstract
Dehydration of guaiol and the epimeric dihydroguaiols in the presence of many acidic dehydrating agents has been studied and the products characterized by GLC, spectroscopic analysis and by chemical transformations. The most interesting dehydration products are Bates' guaioxide (VIIIa, VIIIb) obtained by perchloric acid-acetic acid dehydration of guaiol (I); a methyl ketone (XIII) having a novel skeleton, obtained by the isomerization of the epoxide prepared from 1β,5β-dihydro-β-guaiene (XIb); and the secondary alcohol (XVI) formed by hydroboration-oxidation of 1α-,5α-dihydro-ε-guaiene (XIIa).
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| ID Code: | 3295 |
| Deposited On: | 11 Oct 2010 09:11 |
| Last Modified: | 18 May 2011 07:39 |
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