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• W2121400972 abstract "Abstract An exploratory study has been made on the SO 3 sulfonation of a number of alkylarenes in [D 2 ]dichloromethane as an aprotic solvent, mostly in the presence of [D 8 ]1,4‐dioxane as a reactivity moderator, in order to obtain information on sulfonic acid and sulfonic anhydride formation. 1,2‐Dimethylbenzene ( 1 ) with 1.0 mol‐equiv. of SO 3 yields predominantly the 4‐sulfonic acid ( 1 ‐4‐S), whereas with 4.0 mol‐equiv. of SO 3 , 18 mol‐% of the corresponding (intermolecular) sulfonic anhydride ( 1 ‐4‐SO 2 ) 2 O is additionally formed. 1,4‐Dimethylbenzene ( 2 ) with 0.8 mol‐equiv. of SO 3 yields predominantly 2 ‐2‐S, whereas with 4.0 mol‐equiv. of SO 3 the sulfonic anhydride ( 2 ‐2‐SO 2 ) 2 O and its 6‐S and 6,6′‐S 2 derivatives are formed, the eventual main product being (6‐S‐ 2 ‐2‐SO 2 ) 2 O. Reaction of 1‐ethyl‐4‐methylbenzene ( 3 ) with 2.0 mol‐equiv. of SO 3 ‐[D 8 ]dioxane at −78 → −40 °C leads to the predominant formation of the 2‐ and 3‐S derivatives in a molar ratio of 26:74, with small amounts of the three corresponding intermolecular anhydrides. Upon performing the sulfonation of 3 at 0 → 22 °C, the relative amounts of the anhydrides are larger, and in addition the 3,5‐S 2 derivatives of the intermolecular anhydrides are formed. The absence of the isomeric 2,6‐S 2 derivative is ascribed to the buttressing effect of the 2‐sulfo on the 1‐ethyl group, hampering the sulfonation at C(6). Reaction of diphenylmethane ( 4 ) with 4.2 mol‐equiv. of SO 3 at −20 → 25 °C yields initially 4 ‐4′‐S and subsequently 4 ‐4′,4″‐S 2 . Sulfonation of 1,2‐diphenylethane ( 5 ) with 4.0 mol‐equiv. of SO 3 at −78 → 22 °C for 4.5 h leads mainly to the cyclic dimeric disulfonic anhydride [ 5 ‐4′,4″(‐SO 2 ) 2 O] 2 , which upon hydrolysis affords 9% of 5 ‐2′,4″‐ and 91% of 5 ‐4′,4″‐S 2 . However, sulfonation of 5 at 0 → 22 °C for ca. 0.8 h was found to lead to the formation of the intermolecular sulfonic anhydride (4′‐S‐ 5 ‐4″‐SO 2 ) 2 O. On sulfonation of 1,2‐di‐ p ‐tolylethane ( 6 ) with 1.0 mol‐equiv. of SO 3 , only ca. 20% of the substrate was sulfonated to give, after hydrolysis, 3% of the 2′‐ and 12% of the 3′‐sulfonate, whereas with 4.0 mol‐equiv. of SO 3 the initial monosulfonic acids are almost completely converted to yield the 2′,3″,5″‐S 3 , 3′,3″,5″‐S 3 , and 3′,3″,5′,5″‐S 4 ." @default.
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• W2121400972 date "1997-11-01" @default.
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• W2121400972 title "Aromatic Sulfonation, 131. Formation of Sulfonic Acids and Sulfonic Anhydrides in the Sulfur Trioxide Sulfonation of Some Dialkylbenzenes and 1,ω-Diarylalkanes" @default.
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• W2121400972 doi "https://doi.org/10.1002/jlac.199719971109" @default.
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