An Easy Route to Aziridine Ketones and Carbinols

N,N-Dimethylaziridine-2-carboxamides react with organolithium reagents yielding 2-aziridinylketones. The reaction with one equivalent of organolithium compound is selective to amide carbonyl at a low (−78 °C) temperature. These ketones, in reaction with organolithium reagents, give symmetrical and unsymmetrical aziridinyl carbinols. The usage of excess phenyllithium may serve as a special N-Boc-protecting group cleavage method for acid-sensitive substrates.

Efficient Preparation of Cyclic α-Alkylidene β-Oxo Imides by Using a Flow Microreactor System

Successful transformations of 3-iodo-1-methyl-5,6-dihydropyridin-2(1H)-one into its derivatives by a halogen–lithium exchange and subsequent reactions in a flow microreactor system are described. The methylation of the organolithium compound generated from 3-iodo-1-methyl-5,6-dihydropyridin-2(1H)-one in the flow microreactor system afforded the desired methylated product in 68% yield, whereas the yield of the corresponding batch reaction was 23%. This superiority of the flow microreactor system was further emphasized in the reaction of the organolithium compound with methoxycarbonyl isocyanate, which gave the desired imide in 78% yield by using the flow microreactor system whereas the yield of the corresponding batch reaction was only 2%. The established flow microreactor system was also effectively used for the reaction of the organolithium compound with phenyl isocyanate to afford the desired product in 52% yield.

NCO-Chelated organoantimony(III) and organobismuth(III) dichlorides: Syntheses and structures

The novel NCO chelating ligand L, 1-CH2N(CH3)2-3-CH2OCH3-C6H4, was prepared in four steps from commercially available m-tolunitrile in a good yield. Successful lithiation of this ligand was achieved by the reaction with n-BuLi in hexane. Using of this in situ prepared organolithium compound LLi in the reactions with MCl3 (M = Sb, Bi) in 1:1 molar ratio led to isolation of the desired mono-organocompounds MLCl2 (M = Sb (1), Bi (2)). Their structures were studied both in solution (NMR) and in the solid state (X-ray diffraction), and were compared with those of the NCN- and OCO-chelating analogues.