Decomposition of vinyl ethers by alkalide K−, K+(15-crown-5)2 via organopotassium intermediates

π(Arene) versus donor ligand complexation in the formation of the heterobimetallic lithium–potassium dianion of (S)-N-(α-methylbenzyl)allylamine

“…The high reactivity of 1 became quite apparent through the rapid decomposition which occurred in deuterated thf solution on preparing samples for variable temperature NMR studies. This supports recent [10] and earlier studies [11] that saturated ethers are extremely vulnerable to highly carbanionic potassium reagents even at very low temperatures, suggesting at least one reason why the crystalline complex was so very difficult to obtain and isolate intact from the reaction mixture.…”

Electron-Transfer Processes Mediated by Alkalides: A Critical Approach

“…Regiochemistry of the reaction of K − with aromatic ethers is shown in Table 1 The course of K − , K + (15C5) 2 reactions with aliphatic and aliphatic-aromatic ethers has been presented in several articles [37,83,95,104]. These reactions were also regioselective.…”

“…Reactions of alkalides with ethers have been investigated in details by several authors [37,67,94,[99][100][101][102][103][104][105]. The regioselectivity of ether bond cleavage was the most important aspects of those studies.…”

Chemical Methods for Ether‐Bond Cleavage by Electron‐Transfer Reagents

“…[74] The direction of the cyclic ether bond cleavage in some monosubstituted oxiranes is presented in Table 2. [74] The direction of the cyclic ether bond cleavage in some monosubstituted oxiranes is presented in Table 2.…”

“…[14,74,89] However, in a system containing oxiranes they can react not only with the crown ether but also with the oxirane molecule, or they undergo β-or γ-elimination. [14,74,89] However, in a system containing oxiranes they can react not only with the crown ether but also with the oxirane molecule, or they undergo β-or γ-elimination.…”