Influence of structural features of tri-functionalized aryl phosphates on the outcome of the SRN1 process with stannyl anions: a DFT study

Viviana B. Dorn; Gustavo F. Silbestri; María T. Lockhart; Alicia B. Chopa; Adriana B. Pierini

doi:10.1039/C3NJ40814K

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Influence of structural features of tri-functionalized aryl phosphates on the outcome of the S_RN1 process with stannyl anions: a DFT study†

Viviana B. Dorn,*^a Gustavo F. Silbestri,^a María T. Lockhart,^a Alicia B. Chopa ‡*^a and Adriana B. Pierini^b

Author affiliations

* Corresponding authors

^a INQUISUR, Departamento de Química, Universidad Nacional del Sur, Avenida Alem 1253, 8000 Bahía Blanca, Argentina
E-mail: vdorn@uns.edu.ar
Fax: +54 291 459 5187
Tel: +54 291 459 5187

^b INFIQC, Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Haya de la Torre y Medina Allende, 5000 Córdoba, Argentina

Abstract

Under irradiation, 1,3-bis(diethoxyphosphoryloxy)-4-chlorobenzene (2), 1,4-bis(diethoxyphosphoryloxy)-3-chlorobenzene (3) and 1,3-bis(diethoxyphosphoryloxy)-5-chlorobenzene (4) react with trimethyltinsodium (1) in liquid ammonia giving entirely different distribution of stannylated products. These differences are explained through theoretical DFT studies. Experimental evidence for the involvement of an S_RN1 mechanism was obtained.

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Article information

DOI: https://doi.org/10.1039/C3NJ40814K
Article type: Paper
Submitted: 07 Sep 2012
Accepted: 28 Jan 2013
First published: 28 Jan 2013

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New J. Chem., 2013,37, 1150-1156

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Influence of structural features of tri-functionalized aryl phosphates on the outcome of the S_RN1 process with stannyl anions: a DFT study

V. B. Dorn, G. F. Silbestri, M. T. Lockhart, A. B. Chopa and A. B. Pierini, New J. Chem., 2013, 37, 1150 DOI: 10.1039/C3NJ40814K

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