Abstract
Abstract : The reactions of trimethyl phosphite were investigated with a series of nucleophiles. Products, branching ratios, and reaction rate constants are reported. Reactions generally proceed through an ion-dipole complex (Z-. (CH3O) 3P), to a phosphoranide anion intermediate, (CH3O)3PZ-), to displacement of methoxide to form a new ion-dipole complex (CH3O-(CH3O)2PZ). If an additional acidic hydrogen is available on the nucleophile, the major products result from proton abstraction by methoxide: (CH3O-.(CH30)2PYH) yield (CH30)2PY-+CH3OH. While the displacement of methoxide from phosphorus is sufficiently endothermic, a competing attack at carbon by the original nucleophile occurs: (HY-.(CH3O)3P) yields CH3YH+ (CH3O)2Po-. Nucleophiles without an additional acidic hydrogen react similarly, but the final reaction products result from 1) SN2 reaction of methoxide, 2) SN2 reaction of the original nucleophile, and 3) stabilization of the phosphoranide intermediate, and 4) expulsion of methoxide from the ion- dipole complex. Reaction mechanisms are discussed in terms of the nature of the nucleophiles, the observed products, and the thermodynamics of the displacement reaction. Originator-supplied keywords include: Flowing afterglow; Trimethyl phosphite; Reaction mechanisms; Phosphorous; and Nucleophilic displacement.
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
