Selective cleavage of the linear ether bond in benzyl glycidyl ether and triphenylmethyl glycidyl ether by potassium alkalide as two-electron-transfer reagent

C−O and Not C−C Bond Cleavage Starts the Polymerization of β-Butyrolactone with Potassium Anions of Alkalide

“…It means that K - was in the excess during the reaction. That could lead to wrong conclusions because of possible side reactions between potassium anions and primary reaction products. − In fact, the benzylated derivative of potassium tetraethylene glycoxide vinyl ether is, for example, identified in the reaction mixture when β-butyrolactone was dropped into the solution of 1 , i.e., at the excess of potassium anions.…”

“…A mixture of dipotassium alkoxides derived from the crown ether destruction by K - is formed in this case . Moreover, 1 was successfully employed in the study of the ring opening reaction in several monosubstituted oxiranes − and other cyclic ethers. , Organometallic compounds were formed in all those processes as intermediates of an extreme reactivity. , …”

Formation of Radical Anions and Not Deprotonation Starts the Reaction of γ-Butyrolactone with Potassium Anions

“…The potassium anion has been known as an electron-transfer reagent. It transfers two electrons to the acceptor molecule in two steps, giving finally the potassium cation as it was proved in the excellent work of Perrin and accepted in other papers. − Therefore, K - cannot behave as a nucleophile and, consequently, cannot be able to deprotonate γ-lactone. Furthermore, alkalide K - , K + (18-crown-6) already decomposes autocatalytically to a large extent during its preparation at room temperature .…”

“…Unexpectedly, 8 did not react with 15-crown-5. The benzylated product of the crown ring opening, i.e., tetraethylene glycol benzyl vinyl ether, was not identified in the reaction mixture, although it was observed in several processes with the participation of organopotassium compounds. − , …”