Abstract

The new P—N bonded phosphino- and phosphinatopyrazoles [Formula: see text][Formula: see text] and (C2H5)2P(pz) and the arsenic derivative (pz)3As have been prepared and characterized (pz = pyrazolyl, Me2pz = 3,5-dimethylpyrazolyl).The reactivity of the P—N bond in phosphinopyrazoles towards electrophiles and nucleophiles is discussed. HCl, H2O, CH3OH, and BCl3 cleave the P—N bond, presumably via attack at the 2-N site. BF3 forms 1:1 adducts bonded to phosphorus which are reasonably stable in the solid state. CH3I forms a phosphonium salt with diphenyl(pyrazolyl)phosphine while other members of the series do not react. All members are inert toward CS2. Nucleophiles like sodium methoxide or phenyllithium displace the pyrazolyl moiety by attack at the phosphorus. Comparisons are made with the P—N bond in dialkylaminophosphines.

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