54006-08-5Relevant academic research and scientific papers
Synthesis of P-Substituted 5- And 6-Membered Benzo-Phostams: 2,3-Dihydro-1 H-1,2-benzazaphosphole 2-Oxides and 2,3-Tetrahydro-1 H-1,2-benzazaphosphinine 2-Oxides
Sabourin, Axel,Dufour, Jeremy,Vors, Jean-Pierre,Bernier, David,Montchamp, Jean-Luc
, p. 14684 - 14694 (2021/10/25)
Several approaches were developed for the preparation of phosphorus-substituted 5- and 6-membered benzophostams. Carbodiimide-promoted cyclization of zwitterionic aminophosphinates derived from a nitrobenzene precursor accomplished the cyclization in good
REACTIVITY OF THE ACIDS OF TRIVALENT PHOSPHORUS AND THEIR DERIVATIVES. PART IV. THE REACTION OF DIALKYLPHOSPHITE ANIONS WITH NITROBENZYL BROMIDES
Witt, Dariusz,Rachon, Janusz
, p. 33 - 48 (2007/10/03)
The reaction of o-, m- and p-nitrobenzyl bromide with sodium dimethylphosphite as well as sodium diisopropylphosphite in THF and alcohols as the solvent is described.According to the constitution of the starting materials and the solvents used, the formation of the P-C bond, debromination or dimerization occurs.The principal process in o- and p-nitrobenzyl bromide and >P-O- anion systems is believed to be X-philic substitution, the dimer is formed through a secondary process via SET from the nitrobenzyl anion to nitrobenzyl bromide.Electron-transfer and proton-transfer processes in the nitrobenzyl bromide->P-O- systems are also discussed.Key words: o-, m- and p-nitrobenzyl bromides, dialkyl phosphites, Michaelis-Becker reaction, X-philic substitution, SET.
Organphosphorus Compounds. XVIII. Synthesisi of 2-Phenyl-2,3-dihydro-1H-1,2-benzazaphosphole 2-Sulfide by Pyrolysis of (2-Aminobenzyl)phenyldithiophosphonic Acid
Collins, David J.,Drygala, Peter F.,Swan, John M.
, p. 2095 - 2110 (2007/10/02)
Reaction of 2-phthalimidobenzyl bromide (12b) with the dialkyl phenylphosphonites (13a-c) afforded the corresponding alkyl phosphinates (14a-c) which upon hydrazinolysis yielded the respective (2-aminobenzyl)phenylphosphinates (16a-c).Reduction of the phosphinates (16a) or (16b) with lithium aluminium hydride gave (2-aminobenzyl)phenylphosphine (15), characterized by its conversion into crystalline 2,3-diphenyl-1,2,3,4-tetrahydro-1,3-benzazaphosphorine (18). (2-Aminobenzyl)phenylphosphine (15) was heated with sulfur in benzene under reflux for 30 min to give 80percent of (2-aminobenzyl)phenyldithiophosphinic acid (20) which when heated between 100-200 deg in vacuum underwent elimination of hydrogen sulfide to yield 2-phenyl-2,3-dihydro-1H-1,2-benzazaphosphole 2-sulfide (22a).Several other new phosphorus compounds are described.An attempt to prepare a 1H-1,2-benzazaphosphole derivative by photolysis of methyl benzylphosphonic azide (7) was unsuccessful.
