36912-34-2

Upstream product

• 28097-07-6 trans-2-chloro-5-methyl-1,3,2-dioxaphosphorinane-r-5-methyl chloride 2-oxide 
• 1121-70-6 sodium 4-methylphenoxide 
• 74737-10-3 5r-chloromethyl-2-fluoro-5-methyl-[1,3,2]dioxaphosphinane 2t-oxide 
• 106-44-5 p-cresol 

Downstream Products

• 74465-69-3 Dimethyl 2-(chloromethyl)-2-methyl-3-hydroxypropyl phosphate 
• 28097-12-3 cis-2-methoxy-5-(chloromethyl)-5-methyl-2-oxo-1,3,2-dioxaphosphorinane 
• 36912-27-3 trans-2-methoxy-5-(chloromethyl)-5-methyl-2-oxo-1,3,2-dioxaphosphorinane 
• 74737-10-3 5r-chloromethyl-2-fluoro-5-methyl-[1,3,2]dioxaphosphinane 2t-oxide 
• 74737-11-4 5r-chloromethyl-2-fluoro-5-methyl-[1,3,2]dioxaphosphinane 2c-oxide 
• 36912-33-1 cis-2-(p-methylphenoxy)-5-(chloromethyl)-5-methyl-2-oxo-1,3,2-dioxaphosphorinane 
• 36912-31-9 cis-2-<(p-methoxyphenyl)oxy>-5-(chloromethyl)-5-methyl-2-oxo-1,3,2-dioxaphosphorinane 
• 36912-32-0 trans-2-<(p-methoxyphenyl)oxy>-5-(chloromethyl)-5-methyl-2-oxo-1,3,2-dioxaphosphorinane 

Relevant academic research and scientific papers

INVESTIGATIONS OF THE NUCLEOPHILIC DISPLACEMENT AT THE TETRAHEDRAL PHOSPHORUS - KINETIC EFFECTS OF THE NUCLEOPHILE FOR A GIVEN STEREOCHEMISTRY.

A kinetic study of alcoholysis and aminolysis of 2-chloro-2-oxo-1,3,2-dioxaphospholane, 1, shows a rate levelling effect of the nucleophile, where the stereochemistry is retention at phosphorus.On the other hand, the substitutions with inversion of the 2-chloro-2-oxo-1,3,2-dioxaphosphorinane 2, or the diethylchlorophosphate, 3, show a marked influence of the nucleophile upon the reactivity.Furthermore, the large rate increase which has been observed for the hydrolysis of the five-membered ring phosphorus esters compared to phosphates (an oxygen always displaces an oxygen) is not reproduced when the leaving group is different of the nucleophile.We suggest that the mechanistic implications, established in the case of phosphate esters hydrolysis cannot be directly extended to the general case of SN2(P).The mechanism of nucleophilic substitution of P(4) species is better interpreted in terms of HOMO-LUMO interactions between the nucleophile and the substrate, a process now well established in silicon chemistry.

Silicon Phosphorus Analogies. Fluoride Activation of Nucleophilic Displacement at the Tetrahedral Phosphorus: An Example of Nucleophilic Assistance to Nucleophilic Substitution. 3

We report a mechanistic study of the activation of alcoholysis of the P-X bond (X= Cl, F) by F(1-).Cis and trans isomers of 2-halogeno-5-(chloromethyl)-5-methyl-2-oxo-1,3,2-dioxaphosphorinanes, 1 and 2, or their 2-thio analogues, 3 and 4, and epimeric 2-h

Analogies between silicon and phosphorus stereochemistry-II. Influence of the attacking anion upon the stereochemistry of nucleophilic displacement at tetrahedral phosphorus

The stereochemistry of reactions of cyclic halogenophosphates with a representative series of p-substituted aryloxides emphasizes the relative influence of the attacking anion. For a given leaving group, the stereochemistry depends essentially upon the electronic character of the p-substituent and the ion-pair dissociation of the nucleophile. Both stereochemical and kinetic data rule out a cation-assisted mechanism to explain retention at phosphorus. Meanwhile, a comparison between SN2(P) and SN2(Si) suggests similar mechanisms in the two series. Retention and/or inversion are the consequence of two competing reactions of similar energies. The stereochemistry is determined by the factors which affect the approach of the nucleophile to give two initial intermediates of different geometries.