Some 1,2- and 1,3-diacyl glycerols (with acyl groups as stearyl, oleyl, linoleyl, or stearolyl) were synthesized by conventional methods. The diacyl glycerols were esterified with 6-bromo-hexanoic acid to give the corresponding bromo-triacylglycerols (of the type AAB and ABA containing a bromo group at the distal part of the hexanoate chain). The bromo function was transformed to an azide group by reaction of the bromo-triacylglycerols with sodium azide. The resulting azido-triacylglycerols were then reacted with [60]fullerene to give the requisite aza-fullerenoid triacylglycerol of the type ABA or AAB (45-62% yield based on the amount of [60]fullerene reacted). The nitrogen atom attached to the carbon cage formed a "[5,6]open" type aza substructure, which was confirmed by the appearance of 31-32 signals in the region of deltaC 133-148 (carbon shifts of Sp2 carbons of the cage) in the 13C nuclear magnetic resonance spectra. The spectroscopic and mass spectrometric properties of these novel fullerenoid triacylglycerols are reported.

Reactions of methyl 6-azido-hexanoate, 8-azidooctanoate, and 12-azido-dodecanoate with [60]fullerene (1) gave the corresponding aza-[60]fullerene ester derivatives (2a-2c, 22-35% based on the amount of [60]fullerene reacted). The nitrogen atom is bonded to the [60]fullerene cage to yield a "[5,6]-open" type aza substructure. This was confirmed by the appearance of 30-31 sp2 signals at deltac 133-147 in the carbon nuclear magnetic resonance spectra. Reaction of methyl 11-azido-7-undecynoate with [60]fullerene furnished a mixture of aza-[60]fullerene (2d, 53%) and aziridine-[60]fullerene (2e, 38%) ester derivatives. Compound 2e was identified as the "[6,6]-closed" type aziridine-[60]fullerene derivative, which displayed 10 sp2 signals in the region deltac 140-145 and one signal at deltac 85.05 for the sp3 carbons of the cage. Refluxing a solution of compound 2d in toluene for 50 h gave about 50% yield of compound 2e, but not vice versa.

Epoxidation of a conjugated linoleic acid isomerEpoxidation of methyl (9Z,11E)-octadecadienoate (1) with various epoxidizing agents viz. m-chloroperoxybenzoic acid, dimethyl dioxirane, methyltrioxorhenium/hydrogen peroxide, potassium peroxomonosulfate (Oxone, 2KHSO 5 · KHSO 4 · K 2 SO 4 )/tetrahydrothiopyran-4-one, and Novozyme 435/hydrogen peroxide is described. The reactions furnished the corresponding mono-epoxy [methyl (11,12E)-epoxy-(9Z)-octadecenoate (2) and methyl (9,10Z)-epoxy-(11E)-octadecenoate (3)] and a mixture of diastereomers of syn-and anti-diepoxy-stearate [methyl (9,10Z;11,12E)-diepoxystearate (4a-4d)], which were identified by a combination of spectroscopic and spectrometric analyses.