Formula: C8H12I2Pt. 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: Diiodo(1,5-cyclooctadiene)platinum(II), is researched, Molecular C8H12I2Pt, CAS is 12266-72-7, about Utilizing Redox-Mediated Bergman Cyclization toward the Development of Dual-Action Metalloenediyne Therapeutics. Author is Lindahl, Sarah E.; Park, Hyunsoo; Pink, Maren; Zaleski, Jeffrey M..
Reaction of 2 equiv of 1,2-bis((diphenylphosphino)ethynyl)benzene (dppeb, 1) with Pt(cod)Cl2 followed by treatment with N2H4 yields the reduced Pt(0) metalloenediyne, I (Pt(dppeb)2, 2). This complex is stable to both air oxidation and metal-mediated Bergman cyclization under ambient conditions due to the nearly idealized tetrahedral geometry. Reaction of 2 with 1 equiv of I2 in the presence of excess 1,4-cyclohexadiene (1,4-CHD) radical trap rapidly and near-quant. generates the cis-Bergman-cyclized, diiodo product II (3, 31P: δ = 41 ppm, JPt-P = 3346 Hz) with concomitant loss of 1 equiv of uncyclized phosphine chelate (31P: δ = -33 ppm). In contrast, addition of 2 equiv of I2 in the absence of addnl. radical trap instantaneously forms a metastable Pt(dppeb)22+ intermediate species, 4, that was characterized by δ = 51 ppm in the 31P NMR (JPt-P = 3171 Hz) and νCC = 2169 cm-1 in the Raman profile, indicating that it is an uncyclized, bis-ligated complex. Over 24 h, 4 undergoes ligand exchange to form a neutral, square planar complex that spontaneously Bergman cyclizes at ambient temperature to give the crystalline product Pt(dppnap-I2)I2 (dppnap-I2 = (1,4-diiodonaphthalene-2,3-diyl)bis(diphenylphosphine)), 5, in 52% isolated yield. Computational anal. of the oxidation reaction proposes two plausible flattened tetrahedral structures for intermediate 4: one where the phosphine core has migrated to a trans-spanning chelate geometry, and a second, higher energy structure (3.3 kcal/mol) with two cis-chelating phosphine ligands (41° dihedral angle) via a restricted alkyne-terminal starting point. While the energies are disparate, the common theme in both structures is the elongated Pt-P bond lengths (>2.4 Å), indicating that nucleophilic ligand substitution by I- is on the reaction trajectory to the cyclized product 5. The efficiency of the redox-mediated Bergman cyclization reaction of this stable Pt(0) metalloenediyne prodrug and resulting cisplatin-like byproduct represents an intriguing new strategy for potential dual-threat metalloenediyne therapeutics.
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