Syntheses of Some Phosphino- and Phosphinatoazoles

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Abstract
The following N-substituted azoles have been prepared: (a) diphenylphosphine derivatives of pyrazole (1a), 3,5,-dimethylpyrazole (1b), 3(5)-methylpyrazole (isomers 2a and 2b), pyrrole (7), imidazole (8), and 1,2,4-triazole (9); (b) diphenylphosphinatopyrazole (4b); (c) dichloro-phosphinopyrazole (5a) and dichlorophosphino-3,5-dimethylpyrazole (5b); (c) 1,1-phenyl-phosphinobis(pyrazole) (3); (d) tris(pyrazolyl)phosphine (6a) and tris(3,5-dimethylpyrazolyl) phosphine (6b). Synthetic methods involved reactions (i-iv): (i) azole with chlorophosphine (1–3, 8, 9) or [Formula: see text] (4a) in ethereal solution with triethylamine as hydrogen halide acceptor; (ii) trimethylsilylazole with phosphorus trichloride (5, 6); (iii) potassium pyrrolide with diphenylchlorophosphine (8); (iv) sulfur oxidation of 1a (4b). Nuclear magnetic resonance spectral assignments are discussed.

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