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Synthesis of New Phosphonium Ylides Containing Thiophene and Furan Rings and Study of Their Reaction with Mercury(II) Halides: Spectral and Structural Characterization
Author(s) -
Sabounchei Seyyed Javad,
Jodaian Vida,
Salehzadeh Sadegh,
Samiee Sepideh,
Dadrass Alireza,
Bayat Mehdi,
Khavasi Hamid Reza
Publication year - 2010
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200900305
Subject(s) - chemistry , phosphonium , ylide , halide , medicinal chemistry , furan , thiophene , solvent , nuclear magnetic resonance spectroscopy , crystal structure , stereochemistry , crystallography , inorganic chemistry , organic chemistry
Abstract Reactions of phosphonium ylides (4‐MeC 6 H 4 ) 3 PCHC(O)(2‐C 4 H 3 S) (tptpy), Ph 3 PCHC(O)(2‐C 4 H 3 O) (fppy), and (4‐MeC 6 H 4 ) 3 PCHC(O)(4‐BrC 6 H 4 ) (bbtppy) with HgX 2 (X=Cl, Br, and I) in equimolar ratios in MeOH as solvent leads to the binuclear products 1 – 3 ( Scheme 1 ). The bridge‐splitting reaction of the binuclear complex [{HgI 2 (bbtppy)} 2 ] ( 3c ) by DMSO yields the mononuclear complex [HgI 2 ⋅(bbtppy) (DMSO)] ( 3d ) ( Scheme 2 ). This bridge‐splitting reaction can also be a method for the synthesis of mononuclear products. C ‐Coordination of the ylide and O ‐coordination of DMSO are demonstrated by a single‐crystal X‐ray‐analysis of the mononuclear complex 3d . Characterization of the obtained compounds was also performed by means of elemental analysis and IR and 1 H‐, 31 P‐, and 13 C‐NMR spectroscopy. A theoretical study of some Hg II complexes with phosphonium ylides is also reported.