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ISSN 00125008, Doklady Chemistry, 2013, Vol. 450, Part 1, pp. 122–126. © Pleiades Publishing, Ltd., 2013. Original Russian Text © A.S. Morkovnik, A.R. Akopova, 2013, published in Doklady Akademii Nauk, 2013, Vol. 450, No. 2, pp. 176–180. CHEMISTRY LowBarrier Concerted Electrophilic Aromatic Substitution under the Action of Sulfur Trioxide A. S. Morkovnik and A. R. Akopova Presented by Academician V.I. Minkin July 2, 2012 Received September 7, 2012 DOI: 10.1134/S0012500813050054 According to recent quantum chemical studies by the inability of sulfur trioxide to form σcom plexes (1) with these arenes, but it produces πcom conducted by Prof. P. Schleyer’s research group [1] plexes 2 (2а for benzene) very readily [1, 2]. For SO , and us [2], the sulfonation of the simplest arenes with structures with σcomplex geometry usually do not sulfur trioxide via bimolecular reaction route proceeds correspond to potential energy minima [1] (cf. data for in a nontrivial manner, namely, via concerted isomer pyrrole and their interpretation [8, 9]). ization of πcomplexes ArH SO (2) into sulfonic The driving force of isomerization of the πcom acids rather than classical electrophilic aromatic sub plexes is C→ Oprototropic process that proceeds stitution with intermediate formation of zwitterionic through cyclic
Doklady Chemistry – Springer Journals
Published: Jun 4, 2013
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