- The orthoester Johnson-Claisen rearrangement of allylic terpenols in the presence of acidic ionic liquid
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A convenient protocol for the synthesis of natural isoprenoid-derived carboxylic esters via reaction of allylic terpenols with triethyl orthoacetate (propionate) in the presence of 1-butyl-3-methylimidazolium hexafluorophosphate, [bmim][PF6] (10 mol%), has been developed. The desired terpene derivatives were prepared in moderate to high yield. The ionic liquid (IL) can be easily separated from the products and repeatedly used up to ten times without reduction in the product yield. Experimental data evidence that HF, generated in situ from the IL, most likely acts as a true catalyst in the Johnson-Claisen rearrangement.
- Kryshtal, Galina V.,Zhdankina, Galina M.,Ignat'ev, Nikolai V.,Schulte, Michael,Zlotin, Sergei G.
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- Synthesis of Natural Geranylhydroquinone Analogs
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Hydroquinone was alkylated by geraniol in the presence of aluminum-phenoxide and -isopropoxide catalysts. The reaction products were isolated and characterized. Several features of the process were determined.
- Chukicheva,Fedorova,Koroleva,Kuchin
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p. 1055 - 1058
(2016/02/18)
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- Alkylation of phenol by nerol in the presence of organoaluminum compounds
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Alkylation of aluminum phenolate by nerol and of phenol by nerol in the presence of the organoaluminum compounds aluminum phenolate and aluminum isopropylate was studied. The reaction products were isolated and characterized. Several features of the proce
- Chukicheva,Fedorova,Koroleva,Kuchin
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p. 535 - 540
(2013/02/23)
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- Reaction of orthoesters with alcohols in the presence of acidic catalysts: A study
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Allylic and benzylic alcohols are converted into corresponding unsymmetrical ethers when reacted with various orthoesters in the presence of montmorillonite KSF at ambient temperature. A detailed study has been undertaken to examine the mechanism and generality of these reactions with regard to various acidic catalysts, which reveal interesting competitive reactions mainly O-acetylation, together with trace amount of dimerized product. The type of the side product and their relative quantity depends upon the nature of the catalyst employed. Furthermore, the low yields of the Claisen rearrangement product obtained from allylic alcohols under heating is rationalized due to the formation of some of these products.
- Sampath Kumar,Joyasawal, Sipak,Reddy,Pawan Chakravarthy,Krishna,Yadav
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p. 1686 - 1692
(2007/10/03)
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- Use of an allylchloride for preparing an aldehyde
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The present invention relates to the use of an allylchloride of the general formula STR1 wherein R is a C1 -C12 alkyl group or a C2 -C12 alkenyl group, which groups may be substituted with one or more substitutents selected from the group consisting of C1 -C4 alkoxy, halogen, unsubstituted phenyl and substituted phenyl; a (trihydrocarbyl)silyl group; a (dihydrocarbyl) (hydrocarbyloxy)silyl group; or a dihydropyran-2-yl group, a tetrahydropyran-2-yl group, a dihydrofur-2-yl group or a tetrahydrofur-2-yl group, which groups may be substituted with C1 -C6 alkyl; for preparing an aldehyde compound via an intermediate alcohol compound. The invention further relates to a new allylchloride.
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- PRENYLATION OF OLEFINS IN NITROMETHANE
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The prenylation of isopentenyl and 3,3-dimethylallyl derivatives could be achieved efficiently with dimethyl vinyl carbinol and a variety of acids in nitromethane.Geraniol and isopentenylacetate led to farnesyl derivatives.
- Julia, M.,Schmitz, C.
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p. 2485 - 2490
(2007/10/02)
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- Phenyl derivatives
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Phenyloxy, phenylsulfinyl, phenylthio, phenylsulfonyl, benzyloxy, benzylthio, benzylsulfinyl, or benzylsulfonyl, alkyl or alkenyl derivatives wherein the alkyl or alkenyl group contains at least 7 carbon atoms which are useful in killing and preventing proliferation of insects by upsetting their hormone balance.
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