The deprotonation of HC(pz) 3 with n-butyllithium followed by reaction with methyl iodide, benzyl bromide and chlorotrimethylsilane produced the respective substituted ligands RC(pz) 3 [R = CH 3 , C 6 H 5 CH 2 , (CH 3 ) 3 Si] in good yield. Analogous chemistry starting with HC(3-Phpz) 3 was only successful in high yield when the deprotonation step was carried out with LiN[Si(CH 3 ) 3 ] 2 , added at low temperature, and led to the syntheses of RC(3-Phpz) 3 [R = CH 3 , (CH 3 ) 3 Si, CH 2 =CHCH 2 , C 6 H 5 CH 2 ]. In contrast, the alcohol derivatives HOCH 2 C(pz) 3 and HOCH 2 C(3-Phpz) 3 were prepared using potassium tert-butoxide for the deprotonation step followed by paraformaldehyde. For HC(3-t-Bupz) 3 , deprotonation with n-butyllithium at low temperature was most successful and led to the syntheses of RC(3-t-Bupz) 3 [R = CH 3 , (CH 3 ) 3 Si, HOCH 2 ]. The compound HOCH 2 C(pz) 3 was converted into t-BuPhCH 2 OCH 2 C(pz) 3 by reaction with sodium hydride and (tertbutyl)benzyl bromide. These synthetic routes have made a variety of functionalized tris(pyrazolyl)methane ligands available for studies of their coordination chemistry.
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