Stereoselective epoxidation of cyclohexa-anellated triquinacenes with iodine/silver(I) oxide as compared to m-chloroperbenzoic acid

Eckrich R, Neumann B, Stammler H-G, Kuck D (1996)
JOURNAL OF ORGANIC CHEMISTRY 61(11): 3839-3843.

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Abstract
Iodine/silver(I) oxide (I-2/Ag2O) reacts highly stereoselectively in the single, double, and triple anti epoxidation of the spherical 1,4,7-triene, 10-methyl-2,3:5,6:8,9-tris(cyclohexano)triquinacene 1. All of the three epoxides 3, 4, and 5 obtained with this reagent contain the epoxy groups at the convex side of the triquinacene framework. The stereochemical course of the epoxidation with I-2/Ag2O is clearly distinct from that observed with m-chloroperbenzoic acid (MCPBA), which gives the same monoepoxide (3) but exclusively anti,syn di- and triepoxides (6-8) bearing at least one epoxy group at the concave side of the triquinacene framework. Epoxidation of the related three-fold 1,4-cyclohexadiene, tris(cyclohexeno)triquinacene 2, with MCPBA occurs similarly to the conversion of 1, whereas I-2/Ag2O reacts with high regioselectivity at the less electron-rich peripheral double bonds of 2 giving triepoxides 12 and 13. The molecular structure of triepoxide 8 has been elucidated in detail by X-ray crystal structure analysis.
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Eckrich R, Neumann B, Stammler H-G, Kuck D. Stereoselective epoxidation of cyclohexa-anellated triquinacenes with iodine/silver(I) oxide as compared to m-chloroperbenzoic acid. JOURNAL OF ORGANIC CHEMISTRY. 1996;61(11):3839-3843.
Eckrich, R., Neumann, B., Stammler, H. - G., & Kuck, D. (1996). Stereoselective epoxidation of cyclohexa-anellated triquinacenes with iodine/silver(I) oxide as compared to m-chloroperbenzoic acid. JOURNAL OF ORGANIC CHEMISTRY, 61(11), 3839-3843.
Eckrich, R., Neumann, B., Stammler, H. - G., and Kuck, D. (1996). Stereoselective epoxidation of cyclohexa-anellated triquinacenes with iodine/silver(I) oxide as compared to m-chloroperbenzoic acid. JOURNAL OF ORGANIC CHEMISTRY 61, 3839-3843.
Eckrich, R., et al., 1996. Stereoselective epoxidation of cyclohexa-anellated triquinacenes with iodine/silver(I) oxide as compared to m-chloroperbenzoic acid. JOURNAL OF ORGANIC CHEMISTRY, 61(11), p 3839-3843.
R. Eckrich, et al., “Stereoselective epoxidation of cyclohexa-anellated triquinacenes with iodine/silver(I) oxide as compared to m-chloroperbenzoic acid”, JOURNAL OF ORGANIC CHEMISTRY, vol. 61, 1996, pp. 3839-3843.
Eckrich, R., Neumann, B., Stammler, H.-G., Kuck, D.: Stereoselective epoxidation of cyclohexa-anellated triquinacenes with iodine/silver(I) oxide as compared to m-chloroperbenzoic acid. JOURNAL OF ORGANIC CHEMISTRY. 61, 3839-3843 (1996).
Eckrich, R, Neumann, B, Stammler, Hans-Georg, and Kuck, Dietmar. “Stereoselective epoxidation of cyclohexa-anellated triquinacenes with iodine/silver(I) oxide as compared to m-chloroperbenzoic acid”. JOURNAL OF ORGANIC CHEMISTRY 61.11 (1996): 3839-3843.
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