6533b837fe1ef96bd12a25df

RESEARCH PRODUCT

Reaction of Tris(2-thienyl)phosphine with Dirhodium(II) Acetate. Orthometalation of a Heteroaromatic π-System and an Unusual Ring Rearrangement

Francisco EstevanNorma SigueroPascual LahuertaKlaus BiegerJulia Pérez-prietoMercedes SanaúSalah-eddine StiribaJulio Lloret

subject

TrisStereochemistryOrganic ChemistryRing (chemistry)TolueneMedicinal chemistryCatalysisInorganic Chemistrychemistry.chemical_compoundAcetic acidchemistryThiophenePhysical and Theoretical ChemistryPhosphine

description

The reaction of tris (2-thienyl)phosphine (1) with dirhodium(II) acetate in a 9:1 refluxing toluene/ acetic acid mixture for 2 h leads to the formation of two metalated compounds. The structure of one of them contained two new orthometalated phosphines in a head-to-head arrangement, and, surprisingly, the metalated thiophene rings, but not the nonmetalated ones, were rearranged to a 3-thienyl structure. Both types of dirhodium compounds were assessed in a catalytic α-diazo ester transformation.

https://doi.org/10.1021/om020976f