In 2015,Fernandez Saez, Nerea; Garcia Lopez, Jesus; Iglesias, Maria Jose; Lopez Ortiz, Fernando published 《Derivatization of (quinolin-8-yl)phosphinimidic amides via ortho-lithiation revisited》.Dalton Transactions published the findings.Formula: C2H4I2 The information in the text is summarized as follows:
The direct ortho-lithiation of N-H containing (quinolin-8-yl)phosphinimidic amides by reaction with 1 equiv of BuLi described by Wang and co-workers was reexamined The multinuclear magnetic resonance (1H, 2H, 7Li, 13C, 15N and 31P) study of the species formed in the monolithiation of N-(tert-butyl)-P,P-diphenyl-N’-(quinolin-8-yl)phosphinimidic amide 5 with BuLi in THF showed that proton abstraction occurred exclusively and quant. at the NH. The combination of the NMR results with a DFT study made it possible to describe the structure of the N-lithiated species 9 as a dimer consisting of an eight-membered ring showing two lithium ions triply coordinated to nitrogen atoms corresponding to the deprotonated amine and aminoquinoline moieties of different monomers. The formation of a polymer featuring the same coordination mode couldn’t be excluded. Optimized conditions for the efficient derivatization of 5 via ortho-lithiation were realized. The reaction of 5 with 2.4 equiv of Me3CLi in THF at -80-25° for 3 h afforded a N,Cortho-dilithiated species that was trapped with electrophiles leading to new functionalized ortho derivatives of 5 in good yields. In addition to this study using 1,2-Diiodoethane, there are many other studies that have used 1,2-Diiodoethane(cas: 624-73-7Formula: C2H4I2) was used in this study.
1,2-Diiodoethane(cas: 624-73-7) is one of organic iodides. Alkyl iodides react at a faster rate than alkyl fluorides due to the weak C-I bond. Iodo alkanes participate in a variety of organic synthesis reactions, which include the SimmonsSmith reaction (cyclopropanation using iodomethane), Williamson ether synthesis, Wittig reaction, Grignard reaction, alkyl coupling reactions, and Wurtz reaction.Formula: C2H4I2
Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com