Paper
Mechanism of the reaction of 3,3-dimethyl-1-trimethylsilyl-2-trimethylsiloxy-1-phosphabut-1-ene with chlorobis(o-phenylenedioxy)phosphorane
Published May 17, 2014 · E. Ishmaeva, D. Chachkov, A. Z. Alimova
Russian Journal of Organic Chemistry
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Abstract
We have recently studied by quantum chemical methods the mechanism of the reaction of 3,3-dimethyl-2-trimethylsiloxy-1-trimethylsilyl-1-phosphabut-1ene (I) with diethyl phosphite [1]. There are no published data on mechanisms of reactions of compound I with electrophilic reagents. We previously reported [2] that compound I reacts with an equimolar amount of chlorobis(o-phenylenedioxy)phosphorane under mild conditions to give the product of electrophilic replacement at the two-coordinate phosphorus atom, 3,3-dimethyl-1-bis(o-phenylenedioxy)-λ-phosphanyl-2-trimethylsiloxy-1-phosphabut-1-ene (III), and chlorotrimethylsilane (Scheme 1). of the initial reactants, intermediate products, transition states, and final products were optimized. The structures localized on the potential energy surface were identified as minima or transition states by calculating the corresponding Hessian matrices (all positive eigenvalues for stable molecules and intermediates or at least one negative eigenvalue for transition states). The
The reaction of 3,3-dimethyl-1-trimethylsilyl-2-trimethylsiloxy-1-phosphabut-1-ene with chlorobis(o-phenylenedioxy)phosphorane produces 3,3-dimethyl-1-bis(o-phenylenedioxy)
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