22685-20-7

Usage

Synthesis Reference(s)

Tetrahedron Letters, 28, p. 6513, 1987 DOI: 10.1016/S0040-4039(00)96903-X

InChI:InChI=1/C8H20NO3P/c1-6-11-13(10,12-7-2)9-8(3,4)5/h6-7H2,1-5H3,(H,9,10)

Upstream product

• 95-31-8 N-(tert-butyl)benzothiazole-2-sulfenamide 
• 762-04-9 Diethyl phosphonate 
• 75-64-9 tert-butylamine 
• 814-49-3 diethyl chlorophosphate 
• 118132-81-3 tert-Butyl-phosphorimidic acid triethyl ester 
• 762-04-9 phosphonic acid diethyl ester 

Relevant academic research and scientific papers

Organophotocatalytic Synthesis of Phosphoramidates

We describe the use of visible light in conjunction with an organic dye for the synthesis of phosphoramidates. Cross dehydrogenative coupling reactions between phosphites and amines are reported using organic dyes and light as catalysts for the first time. It is not only a novel application of organic dyes but also fulfils the requirement of sustainability and green chemistry avoiding the use of chromatographic purification techniques. The product was simply isolated from the reaction mixture via an acid-base work-up procedure, rendering the pure product in good yields.

Phosphoramidate synthesis via copper-catalysed aerobic oxidative coupling of amines and H-phosphonates

The copper-catalysed oxidative coupling of amines and H-phosphonates to produce phosphoramidates has been achieved using CuI as the catalyst and O 2 (present in air) as the sole oxidant.

Phosphoramidate-mediated conversion of carbonyl ligands into isocyanide ligands: A new approach to chiral isocyanide ligands

Metal isocyanides have been used and studied by organometallic chemists for many years and, as a result, they have a rich and interesting chemistry. The nature of metal-free isocyanides and the methods of making isocyanide complexes, however, has resulted

Phosphoramidate-mediated conversion of metal carbonyls into metal isonitriles

The reaction of metal carbonyls with readily-available phosphoramidate anions provides a new route to metal isonitriles; in particular, enantiomerically pure isonitrile complexes are easily accessed by this method.

Evidence for Cyclic Azaphosphiridine Oxide Intermediates in the Methoxide-induced Rearrangements of N-Alkyl α-Chlorophosphonamidates: Formation of Phosphoramidates as well as α-Aminophosphonates

The N-butyl α-chlorophosphonamidates RCHClP(O)(NBut)OMe (R=H, Me, or Ph) react with benzyltrimethylammonium methoxide in tetrahydrofuran-methanol to give two types of rearrangement product, the α-aminophosphonates ButNHCHRP(O)(OMe)2 and the phosphoramidates But(RCH2)NP(O)(OMe)2.For the phosphoramidates it seems necessary to postulate the formation of a cyclic azaphosphiridine oxide intermediate, and its subsequent ring-opening, by nucleophilic attack of methoxide at phosphorus, with cleavage of the P-C bond.The α-aminophosphonates are probably also derived from the azaphosphiridine oxide, by cleavage of the P-N bond.The observation that the proportion of the phosphoramidate (P-C cleavage) increases as R changes from Me to H to Ph accords with this picture, as does the apparent lack of any P-C bond cleavage in the rearrangement of Me2CClP(O)(NHR')OMe (R'=Me or But).

IMINOPHOSPHORANE-MEDIATED TRANSFORMATION OF TERTIARY ALCOHOLS INTO t-ALKYLAMINES AND THEIR N-PHOSPHORYLATED DERIVATIVES

Novel azidation of tertiary alcohols by means of trimetylsilyl azide in the presence of boron trifluoride etherate has been worked out.The Staudinger reaction of crude azides with triethyl phosphite affords the corresponding iminophosphoranes which can be directly transformed into diethyl N-(t-alkyl)phosphoroamidates or t-alkylamine tosylates.

REACTION OF SULFENAMIDES WITH DI-ALKYL AND TRIALKYL PHOSPHITES. AN EFFICIENT SYNTHESIS OF PHOSPHORAMIDATES BY UNUSUAL SUBSTITUTION AT S-N BOND IN (2-BENZOTHIAZOLYL)SULFENAMIDES

Regioselective attack of the trivalent phosphorus atom of dialkyl and trialkyl phosphites on either nitrogen or sulfur atom of sulfenamides has been found.The reaction of phenylsulfenamides with dialkyl phosphites yielded phosphorothiolates, whereas the treatment of (2-benzothiazolyl)sulfenamides with dialkyl and trialkyl phosphites gave phosphoramidates in excellent yields.

Electrosynthesis of heteroatom bonds. 5. Direct cross-coupling of dialkylphosphites with amines by an iodonium ion-promoted electrolytic procedure

An efficient direct cross-coupling procedure of dialkylphosphites with amines by an iodonium ion-promoted electrolysis, givin N-substituted dialkyl phosphoramidates, has been proposed.