Calcium and lithium reductions of epoxides in ethylenediamine. A comparison study

Abstract

89 138 133-13412 hexane-acetone CH2=C(CH3) 93 197-205 89 (5)4 (760) p-ho2cc6h66 80 >360 succinic 85 118 119-120®chloroform pivalic 0 "Known compounds were confirmed by MS and also by comparing their IR's with those found in the literature. 6 New Compound: IR (KBr) 3430 (br, OH), 1785 and 1730 (C=0, ánhydride), 1210 cm-1; MS, m/z 314 (M+), 165 (HOOCC6H4COO), 149 (C(= 0)C6H4C00H), and 104 (C(=0)C6H4). Anal. Caled for C16H10O7:

Syntheses in the Isocamphane Series XLI [1]. Derivatives of Epoxyisocamphenilanic Acid, Epoxycamphene, and a New Access to 7-syn-Hydroxycamphene

“…A similar outcome has been reported by Gassman et al for the opening of 2,3-epoxy-1,7,7-trimethylbicyclo[2.2.1]heptane by trimethyl silyl cyanide/ZnI 2 [19]. With Zn/trimethylsilyl chloride/dichloromethane or Li /ethylenediamine [20], a three-component reaction mixture was obtained, although such a reduction of norbornene oxides without rearrangement has been reported [21]. By HPLC it was possible to isolate one single compound pure enough to elucidate its structure by spectroscopic methods.…”

10.1007/s11178-008-2001-z

“…It was shown in [143] that calcium was worthy of competing with lithium. Both metals reduce regioselectively alongside the terminal oxiranes also epoxy derivatives of methylcyclohexene, 9,10-epoxyoctahydronaphthalene, and 8,9-epoxytetrahydroindan.…”

Single Electron Transfer in Radical Ion and Radical-Mediated Organic, Materials and Polymer Synthesis

“…For example, Mg is well-known to organic chemists for Grignard reagents formation . Calcium was used in SET-induced epoxide ring-opening . Sr is also used in the Barbier reaction .…”