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Primary and secondary aminoalkylphosphanes R 2 N-(CH2) m -PH 2  (R 2  = Me 2 , nBu 2 , C 5 H 10 , C 4 H 8 O, 2-(1-Methyl-2-pyrrolidinyl); m = 2, 3, 6, 10, 11; 1-6) or [R 2 N-(CH 2 ) m ] 2 PH (7, R 2  = C 5 H 10 ; m = 2) are accessible by aminoalkylation of PH 3  with ω̃ -chloroalkylamines R 2 N-(CH 2 ) m -Cl in the superbasic medium DMSO/KOH (DMSO = dimethylsulfoxide). By selective N-quaternization of 1, 2, 4-6 with R'I (R' = Me, C n H 2n+1 ; n = 6-8, 12, 16, 18) in the two-phase system CH 2 Cl 2 /H 2 O novel primary phosphanes [R'R 2 N-(CH 2 ) m -PH 2 ] + I -  (11-16f) with quaternary ammonium groups in the alkyl side chain are obtained. The water solubility of 11-16f decreases with increasing chain length (n) of R′ 11 (R = R' = Me; m = 2) shows a trans conformation at the C 2 H 4  bridge according to an X-ray structural analysis. Protonation of 1, 2, 4, 5 with HCl affords the water-soluble hydrochlorides [HR 2 N-(CH 2 ) m -PH 2 ] + Cl -  (19-22). The cationic primary phosphanes 11-16f are stable towards oxygen. By oxidation of 11 with one or two equivalents of H 2 O 2  the primary phosphane oxide [Me 3 N-(CH 2 ) 2 -P(O)H 2 ] + I -  (23) or the phosphonous acid [Me 3 N-(CH 2 ) 2 - P(O)(OH)H] + I -  (23a) are formed. Hofmann degradation of 11 or 16c with KOH yields phosphirane in good yields. Reaction of 1, 2, 4-6 (L) with Fe 2 (CO) 9  at ambient temperature yields stable complexes (CO) 4 FeL (26-30). Under more rigorous conditions Fe 3  clusters (31, 32) with free R 2 N groups are obtained.

zeitschrift für naturforschung b

Wasserlösliche Phosphane, III [1]. Wasserlösliche primäre Phosphane mit Ammoniumgruppierungen NR 2 R' in der Seitenkette -donorfunktionalisierte Amphiphile / Water-Soluble Phosphanes, III [1]. Water-Soluble Primary Phosphanes with Ammonium Groups NR 2 R' in the Side Chain -Donor-Functionalized Amphiphiles