347192-81-8

Upstream product

• 127802-82-8 P-(ethyl)-P,P-(diphenyl)(N-methoxycarbonyl)phosphazene 
• 607-01-2 ethyl-diphenyl-phosphane 

Downstream Products

• 781-33-9 2-methyl-1,1-diphenylpropene 
• 1415025-89-6 (S)-1-phenyl-2-hydrobenzo[c][1,2]azaphosphol-3-one 1-oxide 
• 1415025-87-4 3',3'-dimethyl-1,4',4'-triphenyl-1H-spiro[2,1-benzazaphosphole-1,2'-[1,2]oxaphosphetan]-3(2H)-one 
• 769-57-3 α,β,β-trimethylstyrene 
• 67-64-1 acetone 

Relevant academic research and scientific papers

Synthesis of Pentacoordinated Spiro[44]phosphoranes by Reaction of Cyclic Phosphazenyl Anions with Epoxides: Study of their P-Remote Functionalization and Hydrolysis

The synthesis of a new family of pentacoordinated spiro[4.4]phosphoranes stabilized by the ortho-benzamide bidentate ligand (oBA, -C6H4-2-C(O)NH-) through reaction of C,Cortho-dilithiated phosphazenes with oxiranes is reported. Mixtures of epimers that differ in configuration at the phosphorus atom were obtained with moderate to high yields and diastereoselectivities. C3-Disubstituted derivatives could be separated, which provided access to enantiopure products arising from the reaction with (R)-2-phenyloxirane. Stereomutation was observed by heating the spirophosphoranes at 100 C. Directed ortholithiation of spirophoshoranes followed by electrophilic quench reactions including carbon-based and heteroatom-based electrophiles afforded derivatives functionalized in a remote position with respect to the phosphorus atom. Benzoic acid catalyzed hydrolysis of spirophosphoranes furnished ortho-(γ-hydroxyalkylphosphoryl)benzamides by cleavage of the P O and P N bonds with retention of the phosphorus configuration. In contrast, alkaline hydrolysis led to the formation of γ- hydroxyphosphinic acids and benzamide.

Reactions of lithiated P-diphenyl(alkyl)(N-methoxycarbonyl)phosphazenes with Michael acceptors and aldehydes. Synthesis of 1H-1,2-azaphosphinin-6-ones, β-hydroxy(N-methoxycarbonyl)phosphazenes and 5,6-dihydro-1,3,4-oxazaphosphinin-2-ones

Lithium (N-methoxycarbonyl)phosphazenes add C-regioselectively to DMAD, dimethyl malonate, fumarate, and butylidenmalonate in a [1,4] manner. Only one diastereoisomer is observed with the olefinic electrophiles. With DMAD the initial adduct evolves through cyclocondensation with the CO2Me group of the phosphazene and 1H-1,2-azaphosphinin-6-ones are obtained. Exceptionally, methyl phenylpropiolate reacted exclusively through the carbonyl yielding a mixture of C- and N-acylated compounds. The addition to aldehydes at -80°C affords β-hydroxyphosphazenes diastereoselectively. For lithium α,α-dimethyl(N-methoxycarbonyl)phosphazenes, the intermediate alkoxides cyclocondense at room temperature to 5,6-dihydro-1,3,4-oxazaphosphinin-2-ones.