66778-06-1

Upstream product

• 288-32-4 1H-imidazole 
• 10359-36-1 4-nitro-phenyl diphenyl phosphate 
• 838-85-7 diphenyl hydrogen phosphate 
• 18156-74-6 1-(Trimethylsilyl)imidazole 

Downstream Products

• 10364-94-0 1-benzoylimidazole 
• 403-65-6 diphenyl phosphorofluoridate 
• 18637-83-7 1,1'-oxalyldiimidazole 
• 115918-38-2 phosphoric acid-(2-benzylidenamino-3-indol-3-yl-propyl ester)-diphenyl ester 

Relevant academic research and scientific papers

Chemistry of phosphorus ylides: Part 44 reaction of 1-trimethylsilyl-1H-imidazole with phosphorus reagents. A convenient synthesis of phosphorus silyl imidazoles

The reaction of 1-trimethylsilyl-1H-imidazole with nucleophilic active phosphacumulenes afforded imidazole silyl phosphoranylidenes or imidazole phosphoranylidenes according to the reaction conditions. The reaction of hexaphenylcarbodiphosphorane with 1-trimethylsilyl-1H-imidazole resulted in the formation of silyl phosphoranylidene phosphoranyl imidazole, silyl phosphoranylidene imidazole and triphenylphosphane. Moreover, Lawesson and Japanese reagents afforded imidazole phosphinothioic thioanhydrides.

Single transition state in the transfer of a neutral phosphoryl group between phenoxide ion nucleophiles in aqueous solution

The second-order rate constants (kAro) for reaction of substituted phenoxide ions with 4-nitrophenyl diphenyl phosphate obey a linear equation over a range of 18 substituents with pKArOH values spanning the pKa of the leaving 4-nitrophenolate ion: log kArO =0.53pKArOH -6.6. The linear plot is consistent with a mechanism involving a single transition state or a two-step process with a very reactive intermediate with two almost identical transition states for its formation and breakdown; the value of the exponent (0.53) is also not consistent with a regular stepwise process with a discrete intermediate. The symmetrical reaction of 4-nitrophenolate ion with the 4-nitrophenyl ester is slightly imbalanced whereby bond formation does not keep up with bond fission in the transition state; the transition state, therefore, has some phosphorylium ion character. Transfer of the dielhylphosphoryl group between weakly basic oxyanion nucleophiles is probably a concerted process with a transition state with more of the character of the pentacoordinate intermediate than it has in the corresponding diphenylphosphoryl group transfer.