104975-22-6Relevant articles and documents
OXYGENATED DERIVATIVES OF MENTHATRIENE IN PARSLEY LEAVES
Nitz, Siegfried,Kollmannsberger, Hubert,Spraul, Martin H.,Drawert, Friedrich
, p. 3051 - 3054 (1989)
The analysis of aroma volatiles of parsley revealed the presence of two novel oxygenated p-mentha-1,3,8-tiene derivatives, the amounts of which increase during processing of plant material and deteriorate the typical fresh aroma.The two derivatives, which could be synthesized by means of a dye sensitized photooxygenation reaction, were identified as 1-methyl-4(methylethenyl)-2,3-dioxabicyclooct-5-ene and 4-methyl-7-(methylethenyl)-3,8-dioxatricyclo2-4>octane.Key Word Index - Petroselinum crispum; Umbelliferae; parsley; aroma volatiles; p-mentha-1,3,8-triene; dioxetane; 1-methyl-4-(methylethenyl)-2,3-dioxabicyclooct-5-ene; diepoxide; 4-methyl-7-(methylethenyl)-3,8-dioxatricyclo2-4>octane.
Easy Epoxidation of Monoterpenes from Common Starting Materials
Benitez, Ricardo B.,Bermudez, John H.,Franco, Jaime M.,Rojas, Giovanni
, p. 1086 - 1092 (2020/10/14)
Epoxidation of monoterpenes, α-pinene, β-pinene, limonene, α-terpinene, and (R)-carvone was carried out by the in situ production of a peroxyacid rather than direct addition of such an expensive and difficult to handle chemical. Previous reports showed use of metal catalysts with high yields, while methodologies without catalysts at high temperature showed yields lower than 30%. The authors report a methodology that produces peroxyacetic acid in situ yielding up to 75% pure epoxide at room temperature avoiding the use of catalysts. The products were analyzed by gas chromatography mass spectrometry (GC-MS), and structures were characterized by 1H and 13C nuclear magnetic resonance (NMR).
Ruthenium(II)-Catalyzed Reactions of 1,4-Epiperoxides
Suzuki, Masaaki,Ohtake, Hiroaki,Kameya, Yoshimi,Hamanaka, Nobuyuki,Noyori, Ryoji
, p. 5292 - 5302 (2007/10/02)
The behavior of 1,4-epiperoxides in the presence of transition-metal complexes is highly dependent on the structures of the substrates and the nature of the metal catalysts.Reaction of saturated epiperoxides such as 1,3-epiperoxycyclopentane, 1,4-epiperoxycyclohexane, or dihydroascaridole catalyzed by RuCl2(PPh3)3 in dichloromethane gives a mixture of products arising from fragmentation, rearrangement, reduction, disproportionation, etc.Prostaglandin H2 methyl ester undergoes clean and stereospecific fragmentation to afford methyl(5Z,8E,10E,12S)-12-hydroxy-5,8,10-heptadecatrienoate and malonaldehyde.Bicyclic 2,3-didehydro 1,4-epiperoxides give the syn-1,2:3,4-diepoxides by the same catalyst.The monocyclic analogues are transformed to a mixture of diepoxides and furan products.The stereochemical outcome of the epoxide formation reflects unique differences in the ground-state geometry of the starting epiperoxide substrates.FeCl2(PPh3)2 serves as a useful catalyst for the skeletal change of sterically hindered bicyclic 2,3-didehydro 1,4-epiperoxides to the syn-diepoxides.In addition, the Fe complex best effects the conversion of 1,4-unsubstituted 2,3-didehydro epiperoxides to furans.The Ru-catalyzed reactions are interpreted in terms of the intermediacy of inner-sphere radicals formed by atom transfer of the Ru(II) species to peroxy substrates, in contrast to the Fe-catalyzed reactions proceeding via free, outer-sphere radicals generated by an electron-transfer mechanism.
