Neighboring methoxyl participation in the acid catalyzed methoxylation of methylene-interrupted fatty acids

Chemistry and Physics of Lipids

Volumn 89, Issue 2, 1997, Pages 91-96

  Carballeira, Néstor M ^a   González, María V ^a   Pagán, Mayra ^a  

^a UNIVERSITY OF PUERTO RICO   (Puerto Rico)

Author keywords

Boron trifluoride methanol; Methoxylation; Methyl 10,13 dimethoxyoctadecanoate; Methyl 9,12 dimethoxyoctade canoate; Methyl 9,12 octadecadienoate

Indexed keywords

ALKADIENE; BORON DERIVATIVE; FATTY ACID DERIVATIVE; FLUORIDE; METHANOL;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; GAS CHROMATOGRAPHY; MASS SPECTROMETRY; PRIORITY JOURNAL;

CATALYSIS; FATTY ACIDS; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HYDROCARBONS; HYDROGEN-ION CONCENTRATION; KINETICS; METHANE;

EID: 18844463650     PISSN: 00093084     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0009-3084(97)00062-5     Document Type: Article

References (10)

1. Allred E.L., Winstein S. The role of neighboring groups in replacement reactions. XXVII. 5-Methoxyl participation in some solvolysis reactions. J. Am. Chem. Soc. 89:1967;3991-3997.
2. Blomquist G.J., Howard R.W., McDaniel C.A., Remaley S., Dwyer L.A., Nelson D.R. Application of methoxymercuration-demercuration followed by mass spectrometry as a convenient microanalytical technique for double-bond location in insect-derived alkenes. J. Chem. Ecol. 6:1980;257-269.
3. Christie, W.W., 1993. Preparation of ester derivatives of fatty acids for chromatographic analysis. In: Christie, W. W. (Ed.), Advances in Lipid Methodology-Two, Ch. 2. Oily Press, Scotland, pp. 76-77.
4. Gunstone F.D., Inglis R.P. Application of the oxymercuration-demercuration reaction to long-chain unsaturated esters. Chem. Phys. Lipids. 10:1973;73-88.
5. Gunstone F.D., Inglis R.P. Neighbouring group participation in the oxymercuration-demercuration reaction. Another route to 1,4- and 1,5-epoxides. Chem. Phys. Lipids. 10:1973;89-104.
6. Minnikin D.E., Abley P., Mcquillin F.J., Kusamran K., Maskens K., Polgar N. Location of double bonds in long chain esters by methoxymercuration-demercuration followed by mass spectroscopy. Lipids. 9:1974;135-140.
7. Navarro I., Fabriàs G., Camps F. Possible fatty acyl pheromone precursors in Spodoptera littoralis. Search for 11- and 12-hydroxytetradecanoic acids in the pheromone gland. Lipids. 32:1997;407-412.
8. Vostrowsky, O., Michaelis, K., Bestmann, H.J., 1981. Methoxymercurierung-demercurierung zur bestimmung der doppelbindungspositionen doppelt ungesättigter Lepidopteren-Pheromone. Liebigs Ann. Chem. 1721-1724.
9. Vulliet P., Markey S.P., Tornabene T.G. Identification of methoxyester artifacts produced by methanolic-HCl solvolysis of cyclopropane fatty acids of the genus Yersinia. Biochim. Biophys. Acta. 348:1974;299-301.
10. Winstein S., Allred E., Heck R., Glick R. Neighboring methoxyl participation in solvolytic nucleophilic substitution. Tetrahedron. 3:1958;1-13.