57745-82-1Relevant academic research and scientific papers
Micellar-Induced Selectivity and Rate Enhancement in the Acid-Catalyzed Cyclization and Rearrangement of Monoterpenes. The Solvolysis of Linalyl and Geranyl Acetates
Clark, Benjamin C.,Chamblee, Theresa S.,Iacobucci, Guillermo A.
, p. 1032 - 1036 (1989)
The monoterpene linalyl acetate (1) undergoes acid-catalyzed solvolysis/cyclization at pH 3 in HCl/citrate buffer to yield three major acyclic alcohols, geranol (2), linalool (3), and nerol (4), and one cyclic alcohol, α-terpineol (5).The acyclic/cyclic alcohol ratio is 2.7 in no sodium dodecyl sulfate (SDS) controls after ca. 3 half-lives, compared to 8.5 when the reaction is carried out in a SDS micelle.No micellar rate effect was observed.The SDS-induced selectivity is explained in terms of the micelle-favoring acyclic conformers of linalyl acetate.In contrast to linalyl acetate, solvolysis of geranyl acetate (6) in the SDS micelle at pH 2 gives little product selectivity but yields a 7-fold rate effect relative to no SDS controls.This rate effect results in very different product distributions after 90percent completion of the reaction.The observed SDS rate effect for geranyl acetate is compatible with a difference in solvolysis mechanism for linalyl and geranyl acetate.
CONDENSATIONS BIOMIMETIQUES: EDIFICATION DE SQUELETTES TERPENIQUES A PARTIR DE SYNTHONS ISOPRENIQUES
Babin, Didier,Fourneron, Jean-Dominique,Julia, Marc
, p. 588 - 600 (2007/10/02)
The action of perchloric, trifluoroacetic and formic acids on the 1,1-(and 3,3-) dimethylallylic alcohols has been studied.In the presence of formic acid in dichloromethane 2-methyl-3-butene-2-ol (DMVC) has been condensed on the acetate of 3-methyl-3-butene-1-ol (IPA) giving geranylic and lavandulylic type 1,1-adducts.Saponification, dehydration, oxidation and isomerisation of the former type lead to citral.In the same medium, DMVC produces (after saponification) a C10 glycol which upon dehydration produces lavandulol in a convenient way.Geraniol and its acetate have been condensed with low yield on IPA giving farnesylic derivatives.
