Competing Desulfonylation and S_NAR Reactions During Aromatic Poly(Ether-sulfone) Synthesis

References

• Johnson , R. N. and Harris , J. E. 1988 . Encyclopedia of Polymer Science , 2nd Ed. Edited by: Mark , H. F. , Bikales , N. M. , Overberger , C. G. and Menges , G. Vol. 13 , 196 New York : John Wiley and Sons, Inc. .
   Google Scholar
• Atwood , T. E. , Dawson , P. C. , Freeman , J. L. , Hoy , L. R. J. , Rose , J. B. and Staniland , P. A. 1981 . Polymer , 22 : 1096
   Web of Science ®Google Scholar
• Johnson , R. N. , Farnham , A. G. , Callendining , R. A. , Hale , W. F. and Merian , C. N. J. 1967 . J. Poly. Sci. Polym. Chem. Ed. , 5 : 2375
   Web of Science ®Google Scholar
• Hedrick , J. L. , Mohanty , D. K. , Johnson , B. C. , Viswanathan , R. , Hinkley , J. A. and McGrath , J. E. 1986 . J. Polym. Sci. Polym. Chem. Ed. , 24 : 287
   Web of Science ®Google Scholar
• Mani , R. S. , Zimmerman , B. , Bhatnagar , A. and Mohanty , D. K. 1993 . Polymer , 34 : 171 Bhatnagar A.; King B.; Mohanty D. K.Polymer1994, 35, 1111
   Web of Science ®Google Scholar
• Morgan , P. W. and Herr , B. C. 1952 . J. Am. Chem. Soc. , 74 : 4526
   Web of Science ®Google Scholar
• 3b: mp 200–202°C; IR (Solidfilm) 1664, 1660, 1595, 1447, 1398, 1275, 1164, 924, 764 cm−1; 1H NMR (CDCL3, 300 MHz) δ 8. 12–7. 85 (m, 18H); 13C NMR (CDCl3, 75 MHz) δ 194. 9, 143. 9, 143. 1, 136. 3, 133. 3, 130. 5, 130. 1, 128. 6, 127. 9
   Google Scholar
• mp 74–76°C; IR (Solid film) 1658, 1592, 1497, 1277, 1245, 1169, 976, 748 cm−1; 1H NMR (CDCl3, 300 MHz) δ 7. 83–6. 69 (m, 13H), 1. 34 (s, 9H); 13C NMR (CDCl3, 75MHz) δ 195. 5, 162. 0, 153. 0, 147. 6, 138. 1, 132. 4, 132. 1, 131. 7, 129. 8, 128. 2, 126. 9, 119. 7, 116. 9, 34. 5, 31. 5.
   Google Scholar
• mp 138- 140°C; IR (solid film) 2961, 1654, 1593, 1500, 1242, 1170, 928, 766 cm−1; 1NMR (CDCl3, 300 MHz) δ 7. 79 (m, 4H), 7. 40 (m, 4H), 7. 02 (m, 8H); 13C NMR (CDCl3, 75 MHz) δ 194. 3, 161. 7, 153. 1, 147. 5, 132. 2, 130. 9, 126. 8, 119. 6, 116. 9, 34. 4, 31. 5.
   Google Scholar
• Allcock , H. R. , Lampe and Contemporary , F. W. 1990 . Polymer Chemistry , 25 Prentice Hall .
   Google Scholar
• Otto , R. 1886 . Chem. Ber. , 19 : 2425
   Google Scholar
• Ingold , C. K. and Jessop , J. A. 1930 . J. Chem. Soc. , : 708
   Google Scholar
• Loudon , J. D. 1935 . J. Chem. Soc. , : 537
   Google Scholar
• Levi , A. A. and Smiles , S. 1932 . J. Chem. Soc. , : 1488
   Google Scholar
• Simpkins , N. S. 1993 . Sulphones in Organic Synthesis , Edited by: Baldwin , J. E. and Magnus , P. D. Vol. 10 , Pergamon : Tetrahedron Organic Chemistry Series . Ch. 9
   Google Scholar
• Cerfontain , H. 1968 . “ Mechanistic Aspects in Aromatic Sulfonation and Desulfonatioon ” . Interscience . Ch. 15
   Google Scholar
• Polymer , 11 was characterized by 1H NMR and 13C NMR. According to the 13C NMR, it is very likely that polymer chains are hydroxyl terminated. The intrinsic viscosity value and the relatively low Tg are indicative of the moderate molecular weight nature of 11
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• 11: IR(solid film) 3059, 2969, 1659, 1591, 1499, 1277, 1244, 1169, 1014, 929, 731 cm−1. 1H NMR(CDCl3) δ 8. 08(m, 4H), 7. 86(m, 4H), 7. 77(m, 4H), 7. 28 (m, 4H), 7. 00(m, 8H), 1. 72(s, 6H). 13C NMR(CDCl3, 75 MHz) δ 193. 6, 163. 0, 162. 5, 153. 0, 147. 1, 143. 7, 142. 7, 132. 5, 132. 1, 130. 5, 130. 2, 129. 6, 128. 4, 128. 3, 127. 8, 127. 7, 120. 4, 119. 8, 119. 5, 117. 1, 116. 1, 113. 7, 42. 4, 30. 9. Tg = 148 °C (DSC), third heating, heating rate, 10 °C/min. (η) = 0. 4, CHCl3, 25 °C. Tonset = 435 °C (TGA), heating rate, 10 °C/min.
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