Synthese amino-substituierter Phosphinoxyde

Decomposition reactions of hydroxyalkylphosphorus compounds. II. Reaction of benzylbis(.alpha.-hydroxybenzyl)phosphine oxide with benzaldehyde imines

“…Within 2 weeks, 2.54 g (63% yield) of white solid was collected, mp 146-151°. Two recrystallizations from methanolethyl acetate-acetone yielded the analytical sample, 7: mp 160-161°; ir (KBr) 2.97 (NH), 3.15 (hydrogen-bonded OH), 3.32 (aliphatic CH), 8.71 µ (P=0); NMR (CDCI3) 0.98 (s, 9 H, (CH3)3C), 2.85 (m, 2 H, PCH2), 4.34-4.62 (m, 1 H, PCHN), 5.21 (d, J = 3 Hz, 0.6 H, PCHO), 5.57 (d, J = 11 Hz, 0.4 H, PCHO), 6.67-7.67 (m, 15 H, aromatics). The NMR spectrum showed 7 to be an isomeric mixture.…”

“…Solid slowly began to precipitate and 1.88 g (46% yield) was collected which had mp 120-145°. Recrystallization from acetone gave the analytical sample, 10: mp 146-148°; ir (KBr) 3.0 (shoulder, NH), 3.06, 3.15, and 3.22 (hydrogen-bonded OH), 3.35 (aliphatic CH), 8.68 Hz, 0.5 H, PCHO), 6.67-7.67 (m, 15 H, aromatics); the assignments were made on the D20-exchanged spectrum. In the earlier publica-tion only one pure isomer was obtained.…”

“…Within 2 weeks, 1.13 g (43% yield) of white solid was collected. Recrystallization twice from methanol-water afforded the analytical sample, 13: mp 145-147°; ir (KBr) 3.02 (NH), 3.25 (aromatic CH), 3.49 (aliphatic CH), 8.59 and 8.67 µ (P=0); NMR (CDCI3) 2.5-4.5 (m, 10 H, PCH2, NCH2, NH, PCHN), 6.9-7.6 (m, 25 H, aromatics), two protons were lost from the 2.5-4.5 region on D20 exchange. There are significant differences between 13 and the same product formed in the primary amine reaction.…”

Organophosphorus Complexones

“…The above reaction was subsequently extended by the same workers to dialkyl thiophosphites 80 , diaryl phosphites 81 , arylphosphonous esters 64 , and diarylphosphine oxides 82 , compounds capable of diad tautomerism. The respective products were a -aminoalkylphosphonothioic esters, α-aminoalkylphenylphosphinic esters, andaaminoalkyldiarylphosphine oxides This method has been developed by Moedritzer and Irani 83 , who use phosphorous acid as the phosphorus component.…”

Synthesis of dimethyl 4-thiazolidinylphosphine oxides via addition of dimethylphosphine oxide to 3-thiazolines

“…Dedicated to Professor Louis D. Quin on the occasion of his retirement from the University of Massachusetts. phonic acids and their derivatives [7][8][9][10][11][12][13][14][15][16][17], whereas much less is known about the corresponding ␣-aminophosphine oxides [18][19][20]. In the course of our studies of the addition of dimethylphosphine oxide to C‫ס‬O and C‫ס‬N double bonds [20][21][22][23] and of the synthesis of 4-thiazolidinylphosphonates and derivatives [24][25][26], we now wish to describe the syntheses of several new 3-thiazolines and their dimethylphosphine oxide adducts.…”