US 9,063,416 B2  185  186  TABLE 8  TABLE  9  Compound  Anion  2-45  an-2  2-47  an-2  2-48  an-2  2-49  an-2  2-50  an-2  2-51  an-2  2-53  an-2  2-54  an-2  2-55  an-2  2-56  an-2  2-57  an-2  2-58  an-2  2-59  an-2  2-60  an-2  Cation  ca-45  ca-47  ca-48  ca-49  ca-50  ca-51  ca-53  ca-54  ca-55  ca-56  ca-57  ca-58  ca-59  ca-60  NMR  analysis  $^{1}$H-NMR:  I,  (ppm)- 8.55 (d, 2H,ArH), 8.38 (d, 2H,ArH), 8.32 (d, 2H,ArH), 8.03 (d, 2H,ArH), 7.93-7.97  (m, lH, ArH), 7.82-7.88 (m, SH, ArH), 7.55 (d, 2H, ArH), 4.43(s, 2H, CH2), 2.0l(s, 3H, CH3)  $^{1}$H-NMR:  I,  (ppm) - 4.46 (s, 2H, CH2(C=O)), 4.43(s, 2H, CH2), 3.38-3.58 (m, 4H, CH2SCH2), 1.56-2.33  (m, 24H, Ad+ CH2 + CH3).  $^{1}$H-NMR:  I,  (ppm) - 7.75 (s, 2H,Ar), 4.43(s, 2H, CH2), 3.91-3.96 (m, 2H, CH2), 3.72-3.79 (m, 2H, CH2),  2.29-2.41(m, 4H, CH2), 1.75-2.19(m, 24H, Ar---CH3 + Adamantane).  $^{1}$H-NMR:  I,  (ppm) - 7.82 (m, 2H, Ar), 4.43(s, 2H, CH2), 3.73-3.91(m, 4H CH2), 1.56-2.43(m, 30H,  Ar-CH3 + CH2 + adamantane)  $^{1}$H-NMR:  I,  (ppm) - 8.23 (d, 4H,ArH), 7.98 (d, 4H,ArH), 4.43(s, 2H, CH2), 2.0l(s, 3H, CH3), 1.37 (s,  18H, CH3 oftert-butyl)  $^{19}$F-NMR:  I,  (ppm) - -48.5  $^{1}$H-NMR:  I,  (ppm) - 7.77-7.98 (m, !OH, ArH), 7.64 (s, 2H, ArH), 4.57(s, 2H, CH2O), 4.43(s, 2H, CH2),  2.40 (s, 6H, CH3), 2.02-2.26 (m, 12H, Adamantane + CH3), 1.76 (br s, 6H, Adamantane)  $^{1}$H-NMR:  I,  (ppm)- 8.28 (d, 2H,ArH), 8.11 (d, lH,ArH), 7.86(t, lH,ArH), 7.63-7.Sl(m, 7H,ArH),  4.43(s, 2H, CH2), 2.0l(s, 3H, CH3)  $^{1}$H-NMR:  I,  (ppm)- 8.05 (d, 2H,ArH), 7.74 (d, 2H,ArH), 4.43(s, 2H, CH2), 3.85(s, 3H, S---CH3), 2.0l(s,  3H, CH3), 1.30(s, 18H, t-Bu)  $^{1}$H-NMR:  I,  (ppm) - 8.41(m, 2H ArH), 8.12(d, lH, ArH), 7.73-7.93(m, 2H, ArH), 7.19(d, lH, ArH), 5.23(s,  2H, CH2), 4.95(m, lH, Adamantane), 4.43(s, 2H, CH2), 4.03(m, 2H, CH2S), 3.75(m, 2H, CH2S), 2.27-2.43(m,  4H, SCH2CH2), 1.42-2.01 (m, 17H, Adamantane + CH3)  $^{1}$H-NMR:  I,  (ppm) - 8.42(m, 2H ArH), 8.17(d, lH, ArH), 7.78-7.91(m, 2H, ArH), 7.23(d, lH, ArH), 5.26(s,  2H, CH2), 4.43(s, 2H, CH2), 3.75-4.19(m, 7H, SCH2 + CH3), 2.29-2.60(m, 4H, SCH2CH2), 2.0l(s, 3H, CH3)  $^{1}$H-NMR:  I,  (ppm)- 8.28 (d, 2H,ArH), 8.12 (d, lH,ArH), 7.88 (t, lH,ArH), 7.80 (d, lH,ArH), 7.62-7.74  (m, 5H,ArH), 4.43(s, 2H, CH2), 2.0l(s, 3H, CH3), 1.27 (s, 9H, CH3)  $^{1}$H-NMR:  I,  (ppm) - 7.76-7.90 (m, 12H,ArH), 4.43(s, 2H, CH2), 2.62-2.69 (m, lH, camphane), 2.08-2.26 (m,  8H,Ar---CH3 + camphane), 2.0l(s, 3H, CH3), 1.65-1.72 (m, lH, camphane), 1.19 (s, 3H, CH3), 1.09 (s, 3H,  CH3), 1.04 (s, 3H, CH3).  $^{1}$H-NMR:  I,  (ppm) - 7.76-7.90 (m, 12H,ArH), 5.00 (s, lH, Hyper-lactone), 4.77 (s, 2H, Hyper-lactone),  4.43(s, 2H, CH2), 4.27 (s, lH, Hyper-lactone), 2.94 (s, lH, Hyper-lactone), 2.13 (d, 6H, CH3), 2.11-1.73  (m, 9H, Hyper-lactone), 2.0l(s, 3H, CH3), 1.53 (d, lH, Hyper-lactone).  $^{1}$H-NMR:  I,  (ppm) - 7.72-7.83(m, !OH, ArH), 7.59(s, 2H, ArH), 5.90(d, lH, CH), 4.87-5.05(m, 3H, CH), 4.62- 4.68(m, 2H, CH2), 4.43(s, 2H, CH2), 4.23(m, lH, CH), 2.0l(s, 3H, CH3), 1.75-2.48(m, SH, CH3 + oxosultone)  Compound  Anion  3-1  an-3  3-2  an-3  3-3  an-3  3-4  an-3  3-5  an-3  3-6  an-3  3-7  an-3  3-8  an-3  3-9  an-3  3-10  an-3  3-11  an-3  3-12  an-3  3-13  an-3  3-14  an-3  Cation  NMR  analysis  ca-1  $^{1}$H-NMR:  I,  (ppm)- 7.74-7.90 (m, 15H,ArH), 6.80-7.30(m, 5H, phenyl), 4.62(s, 2H, CH2)  ca-2  $^{1}$H-NMR:  I,  (ppm) - 8.50(d, 2H, ArH), 8.37(d, 2H, ArH), 7.93(t, 2H, ArH), 7.55-7.75(m, 7H, ArH) 6.80- 7.30(m,  SH,  phenyl), 4.62(s, 2H, CH2)  ca-3  $^{1}$H-NMR:  I,  (ppm) - 7.72-7.84(m, 12H, ArH), 7.56(d, 2H, ArH), 6.80-7.30(m, 5H, phenyl), 4.62(s, 2H, CH2),  3.35(s, 3H, CH3)  ca-4  $^{1}$H-NMR:  I,  (ppm)- 7.75-7.86 (m, l0H,ArH), 7.61 (s, 2H,ArH), 6.80-7.30(m, 5H, phenyl), 4.62 (m, 4H,  CH2 + CH2), 2.31 (s, 6H, CH3), 1.49-1.97 (m, 17H,Adamantane)  ca-5  $^{1}$H-NMR:  I,  (ppm) - 7.76-7.82(m, !OH, ArH), 7.59(s, 2H, ArH), 6.80-7.30(m, 5H, phenyl), 4.62(s, 2H, CH2),  ca-6  ca-7  ca-8  ca-9  ca-10  ca-11  ca-12  ca-13  ca-14  4.55(s, 2H, CH2), 2.29(m, 6H, CH3), 1.90-1.93(m, 4H, CH2, cyclopentyl), 1.48-1.75(m, 6H, oyclopentyl), 0.77- 0.Sl(t, 3H, CH3)  $^{1}$H-NMR:  I,  (ppm) - 7.76-7.82(m, !OH, ArH), 7.59(s, 2H, ArH), 6.80-7.30(m, 5H, phenyl), 4.62(s, 2H, CH2),  4.55(s, 2H, CH2), 2.29(m, 6H, CH3), 1.90-2.0S(m, 2H, cyclopentyl), 1.48-1.75(m, 9H, CH3, cyclopentyl)  $^{1}$H-NMR:  I,  (ppm)- 10.05 (s, lH, OH), 7.64-7.87 (m, l0H,ArH), 7.56 (s, 2H,ArH), 6.80-7.30(m, 5H, phenyl),  4.62(s, 2H, CH2), 2.22 (m, 6H, CH3).  $^{1}$H-NMR:  I,  (ppm)- 7.71-7.89 (m, l0H,ArH), 7.59 (s, 2H,ArH), 6.80-7.30(m, 5H, phenyl), 4.62(s, 2H, CH2),  4.53 (s, 2H, CH2), 2.30 (s, 6H, ArCH3)  $^{1}$H-NMR:  I,  (ppm)- 7.75-7.86 (m, l0H,ArH), 7.63(s, 2H,ArH), 6.80-7.30(m, 5H, phenyl), 4.62(s, 2H, CH2),  4.55(s, 2H, CH2), 2.30 (s, 6H, ArCH3), 1.43 (s, 9H, t-Butyl)  $^{1}$H-NMR:  I,  (ppm) - 7.75-7.87(m, !OH, ArH), 7.63(s, 2H, ArH), 6.80-7.30(m, 5H, phenyl), 4.94(t, 2H,  OCH2CF2), 4.84(s, 2H, OCH2), 4.62(s, 2H, CH2), 2.37(s, 6H, CH3)  $^{19}$F-NMR:  I,  (ppm) - -80.4, -119.7  $^{1}$H-NMR:  I,  (ppm) - 7.72-7.83(m, !OH, ArH), 7.59(s, 2H, ArH), 6.80-7.30(m, 5H, phenyl), 4.90(m, lH,  sultone), 4.62-4.68(m, 5H, CH2O + sultone + CH2), 3.83-3.89(m, lH, sultone), 3.43(m, lH, sultone),  1.75-2.49(m, 1 lH, sultone + Ar-CH3)  $^{1}$H-NMR:  I,  (ppm) - 7.74-7.84(m, !OH, ArH), 7.61(s, 2H, ArH), 6.80-7.30(m, 5H, phenyl), 5.42(t, lH, oxo› norbomane), 4.97(s, lH, oxo-norbomane), 4.67-4.71(m, 4H, CH2 + oxo-norbomane), 4.62(s, 2H, CH2), 2.69- 2.73(m, lH, oxo-norbomane), 2.32 (s, 6H,Ar---CH3), 2.06-2.16(m, 2H, oxo-norbomane)  $^{1}$H-NMR:  I,  (ppm) - 7.73-7.85(m, !OH, ArH), 7.59(S, 2H, ArH), 6.80-7.30(m, 5H, phenyl), 4.62(s, 2H, CH2),  3.83(t, 2H, OCH2), 2.33(s, 6H, CH3), 1.45(m, 4H, CH2), 1.29(m, 4H, CH2), 0.87(t, 3H, CH3)  $^{1}$H-NMR:  I,  (ppm) - 8.53 (d, 2H, ArH), 8.27(d, 2H, ArH), 7.95(t, 2H, ArH), 7.74(t, 2H, ArH), 7.20(s, lH, ArH),  6.38(s, lH,ArH), 4.05(t, 2H, cation-OCH2), 4.0l(s, 2H, CH2), 3.23(s, 3H, CH3), 2.86(s, 3H,ArCH3), 1.84(s, 3H,  ArCH3), 1.69(quin, 2H, CH2), 1.37(quin, 2H, CH2), 1.24-1.26(m, 4H, CH2), 0.82(t, 3H, CH3) 