Electric Literature of 1034-39-5. Let’s face it, organic chemistry can seem difficult to learn. Especially from a beginner’s point of view. Like 1034-39-5, Name is Dibromotriphenylphosphorane. In a document type is Article, introducing its new discovery.
Kinetics of Lewis base (LB) complexed primary and secondary sigma-alkyllithiums (RLi) with triphenylmethane (TPMH) are reported. RLis in which one or two LB groups (-OMe, -NMe2, -NMeR) are part of the molecule form, in benzene, intramolecularly complexed tetramers, for example, 24, or dimers, for example, 42. They are used as models for their intermolecular congeners R4Li4 · 4 LB and R2Li2 · 4 LB (LB = NR?3, OR?2). Nonunity reaction orders in [RLi] are in line with reactions via as yet unidentified 1:1 complexes formed in an equilibrium (K(stat. corr.) ? 1) between aggregated RLi and TPMH. In some cases, a tetramer/dimer equilibrium mixture undergoes complexation/reaction. Reaction rates correlate linearly with calculated concentrations of the complexes. Relative rates of complexes range from 1 [prim-R4Li4 · 3 LB · TPMH (presumed)] to 4250 [sec-R2Li2 · 3LB · TPMH (presumed)]. A major role in the reactivity enhancement owing to LB-induced conversion of tetramers into dimers is ascribed to increased LB participation in LB-richer dimer transition states. Amine and ether complexes have practically equal reactivities. Lithiation of TPMH by dimeric RCH2Li is retarded by a factor of 24000 if a silyl group is linked to the alpha-carbon.
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Reference：
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate