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Reaction of Elemol with Acetic acid –Perchloric acid: Characterization of a novel oxide and (+)-β-cyperone

DRS at CSIR-National Institute of Oceanography

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Title Reaction of Elemol with Acetic acid –Perchloric acid: Characterization of a novel oxide and (+)-β-cyperone
 
Creator Wahidullah, S.
Govenkar, M.B.
Paknikar, S.K.
 
Subject elemo
elemoxide
perchloric acid
(+)- β-cyperone
 
Description The minor unidentified compounds of acetic acid- perchloric acid dehydration of elemol (1) have been fully characterized. The structure and relative stereochemistry as shown in (2) of the less polar fragrant compound named as elemoxide was deduced by 1D and 2D NMR data including carbon-carbon connectivity, NOE and NOESY experiments. The absolute stereochemistry was established as 3S,3aR,7aR-6-isopropyl-1,1,3,3a-tetramethyl 1,3,3a,4,7,7a hexahydro isobenzofuran (2) on the basis of its preparation from elemol 1.(+)-b-cyperone (3), a known sesquiterpene, has also been identified as a minor product of the reaction. Plausible mechanistic explanation for the formation of elemoxide (2) and (+)-b-cyperone (3) presented.
 
Date 2006-06-15T10:53:02Z
2006-06-15T10:53:02Z
2006
 
Type Journal Article
 
Identifier Helvetica Chimica Acta, Vol. 89, 496-501
http://drs.nio.org/drs/handle/2264/121
 
Language en
 
Rights 2006 Verlag Helvetica Chimica Acta AG, Zurich
 
Format 226216 bytes
application/pdf
 
Publisher Springer-Verlag