Page 21 of 31
The Journal of Organic Chemistry
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2.52-2.69 (m, 2H), 2.80-2.89 (m, 2H), 6.75 (d, J = 7.6 Hz, 1H), 6.85 (d, J = 7.6 Hz, 1H), 6.99-7.04
(m, 1H), 7.07-7.12 (m, 1H), 7.15-7.22 (m, 2H), 7.26-7.37 (m, 3H), 7.40-7.45 (m, 1H), 7.47-7.53
(m, 2H), 7.56-7.60 (m, 2H). 13C{1H} NMR (100 MHz, CDCl3, TMS) δC 4.2, 11.5, 31.1, 75.7,
105.5, 119.0, 120.3, 121.9, 123.0, 126.0, 126.1, 127.5, 127.8, 128.4, 128.5, 128.9, 134.8, 140.2,
140.6, 143.7, 144.4, 145.6, 146.9, 151.4. IR (neat) 3070, 3055, 3018, 2961, 2916, 2848, 1449,
1442, 1169, 1011, 869, 765, 754, 742, 731, 693 cm-1. HRMS (DART-FTICR) m/z: [C26H21I2]
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[M+H]+ Calcd for C26H21I2 586.9727; found 586.9727.
+
2-iodo-2'-(2-iodoethyl)-3-phenyl-3'-(m-tolyl)-1,1'-spirobi[indene] (2l). A white solid. 103 mg,
o
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78% yield. m.p. 122-124 C. H NMR (400 MHz, CDCl3, TMS) δH 2.46 (s, 3H), 2.54-2.62 (m,
1H), 2.65-2.77 (m, 2H), 2.81-2.90 (m, 1H), 6.81 (d, J = 7.2 Hz, 1H), 6.99 (d, J = 7.6 Hz, 1H),
7.07-7.16 (m, 2H), 7.22-7.29 (m, 4H), 7.30-7.35 (m, 3H), 7.38-7.44 (m, 1H), 7.44-7.50 (m, 1H),
7.51-7.56 (m, 2H) , 7.59-7.64 (m, 2H). 13C{1H} NMR (100 MHz, CDCl3, TMS) δC 3.3, 21.6, 32.0,
75.7, 105.1, 120.5, 120.6, 122.3, 123.2, 125.7, 126.2, 126.3, 127.7, 127.9, 128.5, 128.6, 128.7,
128.8, 129.0, 129.2, 134.4, 134.8, 138.4, 142.9, 143.7, 144.7, 145.3, 145.7, 146.4, 151.7. IR (neat)
3068, 3057, 3031, 2913, 2851, 1451, 1440, 1175, 764, 756, 744, 715, 704, 696 cm-1. HRMS
(DART-FTICR) m/z: [C32H25I2] [M+H]+ Calcd for C32H25I2 663.0040; found 663.0042.
+
2-iodo-2'-(2-iodoethyl)-3-phenyl-3'-(3-(trifluoromethyl)phenyl)-1,1'-spirobi[indene] (2m). A
white solid. 122 mg, 85% yield. m.p. 134-136 oC. 1H NMR (400 MHz, CDCl3, TMS) δH 2.55-2.66
(m, 1H), 2.67-2.80 (m, 3H), 6.84 (d, J = 7.6 Hz, 1H), 7.03 (d, J = 7.6 Hz, 1H), 7.10-7.21 (m, 3H),
7.23-7.36 (m, 3H), 7.45-7.58 (m, 3H), 7.59-7.77 (m, 5H), 7.82 (s, 1H). 13C{1H} NMR (100 MHz,
CDCl3, TMS) δC 2.7, 31.8, 75.7, 120.0, 120.2, 120.6, 122.5, 123.4, 124.0 (q, J = 271.2 Hz), 124.9
(q, J = 3.8 Hz), 125.6 (q, J = 3.8 Hz), 126.4, 126.8, 127.9, 128.1, 128.6, 128.7, 129.0, 129.4, 131.3
(q, J = 32.1 Hz), 132.3, 134.7, 135.3, 143.8, 144.2, 144.3, 144.6, 144.8, 145.7, 152.0. 19F NMR
(CDCl3, 376 MHz) δ -62.48 (s). IR (neat) 3065, 3021, 2953, 2924, 2853, 1594, 1487, 1453, 1320,
1168, 1119, 1069, 802, 765, 756, 717, 693 cm-1. HRMS (DART-FTICR) m/z: [C32H22F3I2]
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[M+H]+ Calcd for C32H22F3I2 716.9757; found 716.9767.
3-(3,5-dimethylphenyl)-2'-iodo-2-(2-iodoethyl)-3'-phenyl-1,1'-spirobi[indene] (2n). A yellow
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oil. 103 mg, 76% yield. H NMR (400 MHz, CDCl3, TMS) δH 2.42 (s, 6H), 2.54-2.63 (m, 1H),
2.63-2.79 (s, 2H), 2.80-2.94 (m, 1H), 6.81 (d, J = 7.2 Hz, 1H), 6.98 (d, J = 7.6 Hz, 1H), 7.06-7.15
(m, 5H), 7.22-7.29 (m, 3H), 7.30-7.35 (m, 1H), 7.44-7.49 (m, 1H), 7.52-7.57 (m, 2H), 7.59-7.64
(m, 2H). 13C{1H} NMR (100 MHz, CDCl3, TMS) δC 3.4, 21.4, 32.1, 75.7, 105.2, 120.5, 120.6,
122.2, 123.2, 126.2, 126.29, 126.32, 127.7, 127.8, 128.5, 128.6, 128.0, 129.7 ,134.3, 134.8, 138.3,
142.7, 143.7, 144.7, 145.3, 145.8, 146.5, 151.7. IR (neat) 3063, 3018, 2920, 2851, 1599, 1452,
1296, 1170, 1020, 855, 754, 742, 715, 696 cm-1. HRMS (DART-FTICR) m/z: [C33H27I2] [M+H]+
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Calcd for C33H27I2 677.0197; found 677.0192.
2-iodo-2'-(2-iodoethyl)-3'-(4-isopropylphenyl)-3-phenyl-1,1'-spirobi[indene] (2o). A white
solid. 129 mg, 93% yield. m.p. 125-127 oC. 1H NMR (400 MHz, CDCl3, TMS) δH 1.34 (d, J = 6.8
Hz, 6H), 2.57-2.64 (m, 1H), 2.65-2.77 (m, 2H), 2.84-2.91 (m, 1H), 2.96-3.04 (m, 1H), 6.81 (d, J =
7.6 Hz, 1H), 6.99 (d, J = 7.6 Hz, 1H), 7.07-7.17 (m 2H), 7.22-7.30 (m, 3H), 7.32 (d, J = 7.2 Hz,
1H), 7.35-7.41 (m, 2H), 7.43-7.51 (m, 3H), 7.52-7.57 (m, 2H), 7.59-7.64 (m, 2H). 13C{1H} NMR
(100 MHz, CDCl3, TMS) δC 3.4, 24.0, 32.1, 34.0, 75.7, 105.3, 120.5, 120.7, 122.2, 123.3, 126.2,
126.3, 126.9, 127.7, 127.8, 128.5, 128.60, 128.62, 129.0, 131.7, 134.8, 142.7, 143.7, 144.7, 145.4,
145.5, 146.5, 148.7, 151.7. IR (neat) 3060, 3010, 2955, 2916, 2843, 1490, 1451, 1440, 1262, 1171,
1071, 1020, 834, 752, 740, 695 cm-1. HRMS (DART-FTICR) m/z: [C34H29I2] [M+H]+ Calcd for
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