Epoxidation and Hydroxylation of Ethylenic Compounds with Organic Peracids*One of the laboratories of the Bureau of Agricultural and Industrial Chemistry, Agricultural Research Administration, U. S. Department of Agriculture.

Abstract

Oxiranes and alpha‐glycols can be prepared from olefins by a variety of methods. One of the most important and generally applicable of these is the oxidation of ethylenic compounds with organic peracids. Depending on the peracid employed and/or operating conditions either an oxirane or an alpha‐glycol can be obtained in good yield. It is important to note that the oxidation step both in epoxidation and hydroxylation reactions with organic peracids is the conversion of the olefin to the oxirane.

Steroid Derivatives as Potential Antimicrobial Agents against Staphylococcus aureus Planktonic Cells

“…As previously described [6], C16-C17 double bond oxidation of 9-bromotriene acetate (compound 9) with meta-chloroperbenzoic acid (mCPBA) led to the corresponding PYED-1, albeit with uncomplete conversion (47% yield). With the aim to improve the reaction yield, the use of a different organic peroxy acid, i.e., monoperphthalic acid, was investigated [22]. As shown in Figure 2, treatment of compound 9 with phthalic anhydride in the presence of 50% of aqueous H 2 O 2 in refluxing DCM gave, after 24 h, the corresponding brominated epoxide (compound 10) in better yields (82%).…”

Lubricants from renewable energy sources – a review

“…Standard industrial process for epoxidation of vegetable oil is based on in situ epoxidation, in which peracid is generated by reacting acetic or formic acid with hydrogen peroxide in the presence of strong mineral acids such as H 2 SO 4 and H 3 PO 4 (83). Epoxidation is carried out either homogeneous (84)(85)(86) or by using a heterogeneous catalyst (87). In homogeneous catalysis, peracids such as peracetic acid generated in situ by mixing hydrogen peroxide with acetic acid are used to epoxidize vegetable oils.…”

Formation of tricyclo[6.3.0.02,5]undecane derivatives during attempts to make the rumphellatin A–C oxacarbon skeleton

“…Due to the significant difference in the electron density of the two C=C bonds a chemoselective reaction was anticipated, [21][22][23] and this was indeed achieved; when 2 was treated with a 1.2 molar equivalent of m-M A N U S C R I P T A C C E P T E D ACCEPTED MANUSCRIPT Tetrahedron 2 chloroperbenzoic acid, the only product, isolated in 92% yield, turned out to be (9E)-12,12-dimethyl-5-oxatricyclo[8.2.0.0 4,6 ]-dodec-9-en-11-one (3). The compound was obtained as a 20:1 mixture of isomers based on the proton NMR spectrum of the crude product, and from studies of molecular models of the transition states leading to the two isomers, there are reasons to believe that the predominant isomer has anti configuration.…”