319488-99-8

Upstream product

• 127802-82-8 P-(ethyl)-P,P-(diphenyl)(N-methoxycarbonyl)phosphazene 
• 100-39-0 benzyl bromide 
• 823219-40-5 (1-phenylprop-2-yl)diphenylphosphane 
• 1516-56-9 azidoformiate de methyle 
• 607-01-2 ethyl-diphenyl-phosphane 
• 603-35-0 triphenylphosphine 
• 2114-39-8 (2-bromopropyl)-benzene 

Relevant academic research and scientific papers

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.

Olefination reactions through phosphazenes

The first synthesis of di-, tri- and tetrasubstituted alkenes through reaction of lithium P-diphenyl(alkyl)(N-carboxymethyl)phosphazenes with aldehydes and ketones is reported.