Safety of Bromoferrocene. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: Bromoferrocene, is researched, Molecular C10BrFe, CAS is 1273-73-0, about Reactions of haloferrocenes with organolithium compounds. Author is Sonoda, Akio; Moritani, Ichiro.
Reactions of BuLi or PhLi with chloroferrocene (I), 1,1′-dichloroferrocene (II), and bromoferrocene (III) were investigated. I (0.802 g) in 25 ml Et2O treated with 200 millimoles. BuLi in Et2O and quenched with H2O gave 0.033 g ferrocene (IV) and 0.534 g I. Lithiation of 0.870 g I followed by carbonation and esterification afforded 0.398 g Me 2-chloroferrocenecarboxylate (V) and 0.051 g di-Me 2-chloroferrocene-1,1′-dicarboxylate. Similarly I and PhLi gave 21% V. Heating I and PhLi 4.5 hr and quenching with H2O afforded 50% I, 8% IV, and 24% phenylferrocene (V). However no ferrocyne was detected in attempted capture with some dienes. Similarly lithiation of II followed by carbonation and esterification gave meso and racemic forms, m. 117-17.5° and 110-11°, of di-Me 2,2′-dichloroferrocenedicarboxylates in 48% yield. The reaction of III with BuLi at -78° followed by quenching with H2O gave 36% IV and 37% IV, whereas lithiation at room temperature gave 99% IV. Treating III with PhLi also afforded small amount of V. Lithiation at the 2-position is favored in the case of the Cl compound whereas Br-Li exchange is favored in the case of the Br compound I lithiated with BuLi and treated with HgBr2 gave bis(2-chloroferrocenyl)mercury (VI), m. 219-20°. Similarly bis(2,1′-dichloroferrocenyl)mercury was prepared Attempted capture of ferrocyne by heating VI in tetracyclone ended in failure, the product being IV.
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Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com