S. Laschat et al.
(CH2CH2O)2CH2, ArOCH2CH2O), 113.5 (5’-C), 114.6, 116.1 (6-C, 3-C, 2’-
C), 121.9 (6’-C), 133.8, 134.3 (5-C, 1’-C), 145.5, 148.1, 148.5 ppm (3’-C, 4’-
C, 1-C, 2-C); FTIR (film): n˜ = 2926, 2868 (s), 1603 (w), 1495, 1467 (s),
1245, 1192, 1137, 1101, 1042 cmꢀ1 (ms); MS (ESI): m/z: 843.5 [M+ꢀI].
CH2OCH2), 3.93–3.94 (m, 4H; OCH2CH2CH2), 3.99–4.02 (m, 4H; Ar-
OCH2CH2O), 4.22–4.28 (m, 4H; ArOCH2CH2O), 6.55 (d, J2’,6’ = 1.7 Hz,
2H; 2’-H), 6.68 (dd, J6’,5’ = 8.3 Hz, J6’,2’ = 1.7 Hz, 2H; 6’-H), 6.74 (d, J5’,6’
= 8.3 Hz, 2H; 5’-H), 6.93 ppm (s, 2H; 3-H, 6-H); 13C NMR (CDCl3,
125 MHz): d = 14.1 (CH3), 22.7, 26.04, 26.07, 29.2, 29.3, 29.4, 29.44, 29.5,
29.59, 29.63, 29.64, 29.7, 31.91, 31.93 (OCH2(CH2)8CH3), 67.2, 68.0, 69.2,
69.3, 69.4 (OCH2(CH2)8CH3, CH2O(CH2CH2O)2CH2, ArOCH2CH2O),
113.6 (5’-C), 114.6, 116.2 (6-C, 3-C, 2’-C), 121.9 (6’-C), 133.8, 134.3 (5-C,
NaI·5d: 1H NMR (CDCl3, 500 MHz): d = 0.85–0.93 (m, 12H; CH3),
1.24–1.48 (m, 32H; OCH2CH2(CH2)4CH3), 1.62–1.67 (m, 4H;
OCH2CH2CH2), 1.76–1.82 (m, 4H; OCH2CH2CH2), 3.67–3.69 (m, 4H;
OCH2CH2CH2), 3.79–3.80, 3.90–3.92 (2m, 8H; CH2OCH2CH2OCH2-
CH2OCH2), 3.93–3.95 (m, 4H; OCH2CH2CH2), 4.08–4.10 (m, 4H; Ar-
OCH2CH2O), 4.29–4.31 (m, 4H; ArOCH2CH2O), 6.53 (d, J2’,6’ = 1.9 Hz,
2H; 2’-H), 6.67 (dd, J6’,5’ = 8.3 Hz, J6’,2’ = 1.9 Hz, 2H; 6’-H), 6.75 (d, J5’,6’
= 8.3 Hz, 2H; 5’-H), 6.92 ppm (s, 2H; 3-H, 6-H); 13C NMR (CDCl3,
125 MHz): d = 14.08, 14.09 (CH3), 22.6, 25.9, 26.0, 29.1, 29.13, 29.2, 29.4,
31.8, 31.9 (OCH2(CH2)5CH3), 67.1, 67.9, 69.1, 69.2, 69.3, 69.4 (OCH2-
(CH2)5CH3, CH2O(CH2CH2O)2CH2, ArOCH2CH2O), 113.5 (5’-C), 114.5,
116.2 (6-C, 3-C, 2’-C), 121.9 (6’-C), 133.8, 134.3 (5-C, 1’-C), 145.4, 148.1,
148.6 ppm (3’-C, 4’-C, 1-C, 2-C); FTIR (film): n˜ = 2923, 2856 (s), 1601
(w), 1495, 1465 (s), 1243, 1191, 1125, 1101 cmꢀ1 (ms); MS (ESI): m/z:
899.6 [M+ꢀI].
1’-C), 145.5, 148.1, 148.6 ppm (3’-C, 4’-C, 1-C, 2-C); FTIR (film): n˜
=
2918, 2850 (s), 1605 (w), 1496, 1466 (s), 1245, 1193, 1121, 1100 cmꢀ1 (ms);
MS (ESI): m/z: 1179.8 [M+ꢀI].
NaI·5i: 1H NMR (CDCl3, 500 MHz): d
= 0.87–0.89 (m, 12H; CH3),
1.26–1.47 (m, 88H; OCH2CH2(CH2)11CH3), 1.60–1.67 (m, 4H;
OCH2CH2CH2), 1.76–1.82 (m, 4H; OCH2CH2CH2), 3.66–3.68 (m, 4H;
OCH2CH2CH2), 3.79–3.80, 3.90–3.91 (2m, 8H; CH2OCH2CH2OCH2-
CH2OCH2), 3.93–3.95 (m, 4H; OCH2CH2CH2), 4.04–4.06 (m, 4H; Ar-
OCH2CH2O), 4.28–4.30 (m, 4H; ArOCH2CH2O), 6.54 (d, J2’,6’ = 1.9 Hz,
2H; 2’-H), 6.67 (dd, J6’,5’ = 8.2 Hz, J6’,2’ = 1.9 Hz, 2H; 6’-H), 6.75 (d,
J5’,6’ = 8.2 Hz, 2H; 5’-H), 6.93 ppm (s, 2H; 3-H, 6-H); 13C NMR (CDCl3,
125 MHz): d = 14.1 (CH3), 22.7, 26.0, 26.1, 29.1, 29.3, 29.4, 29.5, 29.6,
29.7, 29.8, 31.9 (OCH2(CH2)12CH3), 67.7, 68.4, 69.1, 69.2, 69.5, 69.6
(OCH2(CH2)12CH3, CH2O(CH2CH2O)2CH2, ArOCH2CH2O), 113.3 (5’-
C), 114.9, 116.0 (6-C, 3-C, 2’-C), 121.8 (6’-C), 133.8, 134.1 (5-C, 1’-C),
147.9, 148.4 ppm (3’-C, 4’-C, 1-C, 2-C); FTIR (film): n˜ = 2918, 2850 (s),
1604 (w), 1496, 1467 (s), 1245, 1194, 1121, 1100 cmꢀ1 (ms); MS (ESI):
m/z: 1292.9 [M+ꢀI].
NaI·5e: 1H NMR (CDCl3, 500 MHz): d = 0.87–0.93 (m, 12H; CH3),
1.28–1.48 (m, 40H; OCH2CH2(CH2)5CH3), 1.62–1.68 (m, 4H;
OCH2CH2CH2), 1.76–1.82 (m, 4H; OCH2CH2CH2), 3.66–3.69 (m, 4H;
OCH2CH2CH2), 3.79–3.80, 3.90–3.91 (2m, 8H; CH2OCH2CH2OCH2-
CH2OCH2), 3.92–3.95 (m, 4H; OCH2CH2CH2), 4.08–4.09 (m, 4H; Ar-
OCH2CH2O), 4.29–4.31 (m, 4H; ArOCH2CH2O), 6.53 (d, J2’,6’ = 1.9 Hz,
2H; 2’-H), 6.67 (dd, J6’,5’ = 8.3 Hz, J6’,2’ = 1.9 Hz, 2H; 6’-H), 6.75 (d,
J5’,6’ = 8.3 Hz, 2H; 5’-H), 6.92 ppm (s, 2H; 3-H, 6-H); 13C NMR (CDCl3,
125 MHz): d = 14.1 (CH3), 22.6, 22.7, 26.05, 26.08, 29.2, 29.3, 29.4, 29.44,
31.9 (OCH2(CH2)6CH3), 67.2, 67.9, 69.2, 69.3, 69.4 (OCH2(CH2)6CH3,
CH2O(CH2CH2O)2CH2, ArOCH2CH2O), 113.5 (5’-C), 114.5, 116.2 (6-C,
3-C, 2’-C), 121.9 (6’-C), 133.8, 134.3 (5-C, 1’-C), 145.4, 148.1, 148.6 ppm
(3’-C, 4’-C, 1-C, 2-C); FTIR (film): n˜ = 2924, 2857 (s), 1603, 1562 (w),
1497, 1464 (s), 1244, 1192, 1130, 1102 cmꢀ1 (ms); MS (ESI): m/z: 955.5
[M+ꢀI].
NaI3·5a: M.p. 1208C; 1H NMR (CDCl3, 500 MHz): d = 3.82–3.87, 3.89–
3.91 (2m, 8H; CH2OCH2CH2OCH2CH2OCH2), 4.05–4.06 (m, 4H; Ar-
OCH2CH2O), 4.31–4.33 (m, 4H; ArOCH2CH2O), 5.93 (s, 4H; OCH2O),
6.58–6.61 (m, 4H; 2’-H, 5’-H), 6.69–6.70 (m, 2H; 6’-H), 6.91 ppm (s, 2H;
3-H, 6-H); 13C NMR (CDCl3, 125 MHz): d
= 67.4, 68.4, 69.2, 69.4
(CH2O(CH2CH2O)2CH2, ArOCH2CH2O), 101.0 (OCH2O), 108.1 (5’-C),
110.3 (2’-C), 115.3 (6-C, 3-C), 123.3 (6’-C), 134.5, 134.6 (5-C, 4-C, 1’-C),
145.5, 146.5, 147.3 ppm (1-C, 2-C, 3’-C, 4’-C); FTIR (CDCl3): n˜ = 2877
(ms), 1604 (w), 1499, 1482 (s), 1238, 1172, 1123, 1039 cmꢀ1 (ms); MS
(ESI): m/z: 531.1 [M+ꢀI3].
NaI·5 f: 1H NMR (CDCl3, 500 MHz): d
= 0.87–0.90 (m, 12H; CH3),
1.28–1.47 (m, 48H; OCH2CH2(CH2)6CH3), 1.62–1.67 (m, 4H;
OCH2CH2CH2), 1.76–1.82 (m, 4H; OCH2CH2CH2), 3.66–3.69 (m, 4H;
OCH2CH2CH2), 3.78–3.80, 3.90–3.91 (2m, 8H; CH2OCH2CH2OCH2-
CH2OCH2), 3.92–3.95 (m, 4H; OCH2CH2CH2), 4.07–4.08 (m, 4H; Ar-
OCH2CH2O), 4.28–4.30 (m, 4H; ArOCH2CH2O), 6.53 (d, J2’,6’ = 1.9 Hz,
2H; 2’-H), 6.67 (dd, J6’,5’ = 8.3 Hz, J6’,2’ = 1.9 Hz, 2H; 6’-H), 6.75 (d, J5’,6’
= 8.3 Hz, 2H; 5’-H), 6.92 ppm (s, 2H; 3-H, 6-H); 13C NMR (CDCl3,
[CsI·(5a)2]: M.p. 1448C; 1H NMR (CDCl3, 500 MHz): d = 3.76–3.79 (m,
8H; CH2OCH2CH2OCH2CH2OCH2), 3.91–3.93 (m, 4H; ArOCH2CH2O),
4.17–4.19 (m, 4H; ArOCH2CH2O), 5.93 (s, 4H; OCH2O), 6.58–6.60 (m,
4H; 2’-H, 5’-H), 6.68–6.69 (m, 2H; 6’-H), 6.85 ppm (s, 2H; 3-H, 6-H); 13C
NMR (CDCl3, 125 MHz):
d
=
69.3, 69.7, 70.6, 71.2 (CH2O-
(CH2CH2O)2CH2, ArOCH2CH2O), 100.9 (OCH2O), 108.0 (5’-C), 110.4
(2’-C), 116.5 (6-C, 3-C), 123.3 (6’-C), 133.3, 135.4 (5-C, 4-C, 1’-C), 146.1,
147.2, 148.2 ppm (1-C, 2-C, 3’-C, 4’-C); FTIR (CDCl3): n˜ = 2873 (w),
1601 (w), 1501, 1482, 1455 (s), 1239, 1129, 1039 cmꢀ1 (ms); MS (ESI):
m/z: 1149.2 [M+ꢀI].
125 MHz): d
= 14.1 (CH3), 22.7, 26.06, 26.09, 29.2, 29.3, 29.34, 29.4,
29.46, 29.5, 29.6, 29.7, 31.9, 32.0 (OCH2(CH2)7CH3), 67.4, 68.1, 69.3, 69.4
(OCH2(CH2)7CH3, CH2O(CH2CH2O)2CH2, ArOCH2CH2O), 113.5 (5’-C),
114.7, 116.2 (6-C, 3-C, 2’-C), 121.9 (6’-C), 133.8, 134.2 (5-C, 1’-C), 145.7,
148.1, 148.5 ppm (3’-C, 4’-C, 1-C, 2-C); FTIR (film): n˜ = 2920, 2851 (s),
1602 (w), 1495, 1465 (s), 1244, 1191, 1126, 1100 cmꢀ1 (ms); MS (ESI):
m/z: 1011.6 [M+ꢀI].
[CsI·(5h)2]: 1H NMR (CDCl3, 500 MHz): d = 0.87–0.89 (m, 12H; CH3),
1.26–1.47 (m, 72H; OCH2CH2(CH2)9CH3), 1.62–1.67 (m, 4H;
OCH2CH2CH2), 1.76–1.82 (m, 4H; OCH2CH2CH2), 3.65–3.68 (m, 4H;
OCH2CH2CH2), 3.75–3.78 (m, 8H; CH2OCH2CH2OCH2CH2OCH2),
3.90–3.94 (m, 8H; ArOCH2CH2O, OCH2CH2CH2), 4.19–4.20 (m, 4H; Ar-
OCH2CH2O), 4.22–4.28 (m, 4H; ArOCH2CH2O), 6.54 (d, J2’,6’ = 2.0 Hz,
2H; 2’-H), 6.68 (dd, J6’,5’ = 8.3 Hz, J6’,2’ = 2.0 Hz, 2H; 6’-H), 6.74 (d,
J5’,6’ = 8.3 Hz, 2H; 5’-H), 6.92 ppm (s, 2H; 3-H, 6-H); 13C NMR (CDCl3,
125 MHz): d = 14.1 (CH3), 22.7, 26.0, 26.1, 29.2, 29.3, 29.4, 29.47, 29.5,
29.68, 29.72, 29.73, 29.75, 29.8, 30.9, 31.9 (OCH2(CH2)10CH3), 69.1, 69.2,
69.3, 69.5, 70.3, 70.8 (OCH2(CH2)10CH3, CH2O(CH2CH2O)2CH2, Ar-
OCH2CH2O), 113.3 (5’-C), 116.1, 116.3 (6-C, 3-C, 2’-C), 121.8 (6’-C),
133.6, 134.2 (5-C, 1’-C), 147.7, 147.8, 148.4 ppm (3’-C, 4’-C, 1-C, 2-C);
FTIR (neat): n˜ = 2955, 2918, 2872, 2850 (s), 1603 (w), 1496, 1467 (s),
1250, 1192, 1135 cmꢀ1 (ms); TOF-MS (ES): m/z: 1289.2 [M+ꢀI].
NaI·5g: 1H NMR (CDCl3, 500 MHz): d = 0.87–0.89 (m, 12H; CH3),
1.21–1.46 (m, 56H; OCH2CH2(CH2)7CH3), 1.62–1.67 (m, 4H;
OCH2CH2CH2), 1.76–1.82 (m, 4H; OCH2CH2CH2), 3.66–3.69 (m, 4H;
OCH2CH2CH2), 3.79–3.80, 3.83–3.84 (2m, 8H; CH2OCH2CH2OCH2-
CH2OCH2), 3.93–3.94 (m, 4H; OCH2CH2CH2), 4.09–4.10 (m, 4H; Ar-
OCH2CH2O), 4.30–4.31 (m, 4H; ArOCH2CH2O), 6.52 (d, J2’,6’ = 1.9 Hz,
2H; 2’-H), 6.67 (dd, J6’,5’ = 8.3 Hz, J6’,2’ = 1.9 Hz, 2H; 6’-H), 6.75 (d, J5’,6’
= 8.3 Hz, 2H; 5’-H), 6.93 ppm (s, 2H; 3-H, 6-H); 13C NMR (CDCl3,
125 MHz): d = 14.1 (CH3), 22.7, 26.06, 26.09, 29.2, 29.39, 29.41, 29.48,
29.5, 29.68, 29.71, 29.73, 29.75, 29.79, 31.9 (OCH2(CH2)10CH3), 67.1, 67.9,
69.1, 69.3, 69.4 (OCH2(CH2)10CH3, CH2O(CH2CH2O)2CH2, ArOCH2-
CH2O), 113.5 (5’-C), 114.5, 116.1 (6-C, 3-C, 2’-C), 121.9 (6’-C), 133.8,
134.3 (5-C, 1’-C), 145.4, 148.1, 148.5 ppm (3’-C, 4’-C, 1-C, 2-C); FTIR
(film): n˜ = 2920, 2852 (s), 1603, 1560 (w), 1496, 1466 (s), 1244, 1193,
1121, 1102 cmꢀ1 (ms); MS (ESI): m/z: 1067.7 [M+ꢀI].
[CsI·(5i)2]: 1H NMR (CDCl3, 500 MHz): d = 0.87–0.89 (m, 12H; CH3),
1.26–1.47 (m, 88H; OCH2CH2(CH2)11CH3), 1.57–1.66 (m, 4H;
OCH2CH2CH2), 1.76–1.82 (m, 4H; OCH2CH2CH2), 3.64–3.67 (m, 4H;
OCH2CH2CH2), 3.76–3.78 (m, 8H; CH2OCH2CH2OCH2CH2OCH2),
3.90–3.94 (m, 8H; ArOCH2CH2O, OCH2CH2CH2), 4.19–4.20 (m, 4H; Ar-
OCH2CH2O), 6.54 (d, J2’,6’ = 2.1 Hz, 2H; 2’-H), 6.68 (dd, J6’,5’ = 8.3 Hz,
J6’,2’ = 2.1 Hz, 2H; 6’-H), 6.74 (d, J5’,6’ = 8.3 Hz, 2H; 5’-H), 6.92 ppm (s,
NaI·5h: 1H NMR (CDCl3, 500 MHz): d = 0.87–0.89 (m, 12H; CH3),
1.26–1.47 (m, 72H; OCH2CH2(CH2)9CH3), 1.62–1.67 (m, 4H;
OCH2CH2CH2), 1.76–1.82 (m, 4H; OCH2CH2CH2), 3.66–3.69 (m, 4H;
OCH2CH2CH2), 3.79–3.80, 3.90–3.91 (2m, 8H; CH2OCH2CH2OCH2-
1034
ꢀ 2006 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Chem. Eur. J. 2006, 12, 1026 – 1035