caa a22 4500 465787517 CHVBK 20180323112013.0 cr unu---uuuuu 170327e19900801xx s 000 0 eng 10.1007/BF00297313 doi (NATIONALLICENCE)springer-10.1007/BF00297313 Sulfonation of chlorine-containing polymers: Sulfonation of various model tert -alkyl chlorides [Elektronische Daten] [Robson Storey, Youngkwan Lee] Summary: tert-Alkyl chlorides of the structure R-C(CH3)2Cl, where R-methyl, ethyl, tert-butyl, and neo-pentyl, were reacted with a stoichiometric quantity of acetyl sulfate at room temperature in methylene chloride diluent. Reaction conversion was monitored as a function of time using 1H NMR; structure of the sulfonated products was characterized using 1H and 13C NMR. Reactivity toward sulfonation increased with increasing size of the R group. In all cases the structure of the products was the same as would be expected from sulfonation of the olefin which results from dehydrochlorination of the tert-chloride. The observed behavior was consistent with a mechanism involving dehydrochlorination followed by addition of SO3 to yield a zwitterionic intermediate. Depending upon structure, the zwitterion may either eliminate a proton to form one or more isomeric β,γ-unsaturated sulfonic acids, or it may rearrange to form a five-membered γ-sultone. This chemistry, which is particularly useful in the synthesis of ionomers, represents a direct route to alkyl sulfonic acids when the alkyl halide is the natural starting point in the synthesis. Springer-Verlag, 1990 Storey Robson Department of Polymer Science, University of Southern Mississippi, Southern Station Box 10076, 39406-0076, Hattiesburg, MS, USA aut Lee Youngkwan Department of Polymer Science, University of Southern Mississippi, Southern Station Box 10076, 39406-0076, Hattiesburg, MS, USA aut Polymer Bulletin Springer-Verlag 24/2(1990-08-01), 165-172 0170-0839 24:2<165 1990 24 289 https://doi.org/10.1007/BF00297313 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/BF00297313 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Storey Robson Department of Polymer Science, University of Southern Mississippi, Southern Station Box 10076, 39406-0076, Hattiesburg, MS, USA aut NATIONALLICENCE 700 1- Lee Youngkwan Department of Polymer Science, University of Southern Mississippi, Southern Station Box 10076, 39406-0076, Hattiesburg, MS, USA aut NATIONALLICENCE 773 0- Polymer Bulletin Springer-Verlag 24/2(1990-08-01), 165-172 0170-0839 24:2<165 1990 24 289 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer