Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: Bromoferrocene, is researched, Molecular C10BrFe, CAS is 1273-73-0, about Reactions of haloferrocenes with organolithium compounds.Application In Synthesis of Bromoferrocene.
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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Reference:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com