Studies on the Highly Nucleophilic Triphenylphosphines and their Derivatives

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1. Tris(2.6-dimethoxyphenyl)phosphine oxide. {2,6-(MeO)_2C_6H_3}_3P=O, is highly soluble in water and reacts with acids to form stable hydroxy phosphonium salts. [{2,6-(MeO_2C_6H_3}_3P-OH]X (X= C10_4, BF_4). The salt (X= C10_4) formed stable 1:1 adducts, [{2,6-(MeO)_2C_6H_3}_3P=O, HNR_3]C10_4, with a variety of amines.2. Tris(2,6-dimethoxyphenyl)phosphine sulfide. {2,6-(MeO)_2C_6H_3}_3P=S, reacted with acids to form protonated salts. of which thermolysis in the absence or presence of triphenylphosphine resulted in the un-usual desulfurization to give the tertiary phosphonium salt.3. 2,6-Dimethoxybenzenethiol is a non-smelling, air-stable crystal-line compound with stronger nucleophilicity towards alkyl halides than phSH; the crystallinity of several types of derivative ArSR (R=H, Ar, SAr, CH_2CH_2SAr, CH_2CH_2CH_2SAr) is in the order of Ar=Ph < 2-MeOC_6H_4 < 2.6-(MeO)_2C_6H_3.4. {2,4,6-(MeO)_3C_6H_2}_3P, {2,6-(MeO)_2C_6H_3}_3P and their onium salts were found to be excellent extractants for particular metal ions such as Ca^<3+>and Au^<3+> in hydrochloric acid solution.