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5

Spectral data

5. Spectra

5.1. IR

spectra

5.1.1. Infrared spectrum of 1 5.1.2. Infrared spectrum of 118

(2)

5.1.3. Infrared spectrum of 121

(3)

5.1.5. Infrared spectrum of 127

(4)

5.1.7. Infrared spectrum of 23

(5)

5.1.9. Infrared spectrum of 133

(6)

5.1.11. Infrared spectrum of 151

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5.1.13. Infrared spectrum of 175

5.2. MS

spectra

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5.2.2. Mass spectrum of 118

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5.2.4. Mass spectrum of 126b

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5.2.6. Mass spectrum of 159

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5.2.8. Mass spectrum of 132

(12)

5.2.10. Mass spectrum of 134

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5.2.12. Mass spectrum of 3

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5.3. NMR

spectra

5.3.1.1. 1H NMR spectrum of 1 (CDCl3, 600 MHz) 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm 2.19 1.14 1.28 1.07 1.08 1.12 1.10 1.06 1.05 1.01 1.00 1 O 5.3.1.2. 13C NMR spectrum of 1 (CDCl3, 150 MHz) 230 220 210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm 33 .9 38 .5 42 .6 46 .4 50 .1 52 .0 56 .1 59 .8 13 6. 4 13 7. 8 22 1. 2 1 O O 1 O 1

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5.3.1.3. DEPT spectrum of 1 (CDCl3) 210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm 30.9 31.1 33.9 37.6 38.5 42.6 44.5 46.4 48.3 50.1 52.0 53.1 56.1 59.8 77.2 136.4 137.8 1 O 5.3.1.4. COSY spectrum of 1 (CDCl3) ppm 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 ppm 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 1 O O 1 O 1

(16)

5.3.1.5. HSQC spectrum of 1 (CDCl3) ppm 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 ppm 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 1 O 5.3.2.1. 1H NMR spectrum of 118 (CDCl3, 600 MHz) 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm 1.10 2.09 1.14 1.05 2.18 2.02 1.07 1.05 1.01 1.00 0.97 119 OH H O 1 OH H 118

(17)

5.3.2.2. 13C NMR spectrum of 118 (CDCl3, 150 MHz) 210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm 32 .3 39 .0 42 .3 46 .7 47 .7 51 .6 52 .4 59 .4 77 .5 1 39. 4 1 39. 9 119 OH H 5.3.2.3. DEPT spectrum of 118 (CDCl3) 210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm 32.3 39.0 42.3 46.7 47.7 51.6 52.4 59.4 77.5 139.4 139.9 119 OH H OH H 118 OH H 118

(18)

5.3.2.4. COSY spectrum of 118 (CDCl3) ppm 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 ppm 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 119 OH H 5.3.2.5. HSQC spectrum of 118 (CDCl3) ppm 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 ppm 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 119 OH H OH H 118 OH H 118

(19)

5.3.3.1. 1H NMR spectrum of 121 (CDCl3, 600 MHz) 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm 2.00 1.24 3.07 1.08 1.12 1.08 1.05 1.88 1.00 0.95 0.92 0.94 OAc H 122 5.3.3.2. 13C NMR spectrum of 121 (CDCl3, 150 MHz) 230 220 210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm 21 .3 32 .1 35 .4 41 .8 46 .6 47 .5 49 .5 51 .1 58 .5 78 .5 1 36. 0 1 40. 5 1 71. 1 OAc H 122 OAc H 121 OAc H 121

(20)

5.3.3.3. DEPT spectrum of 121 (CDCl3) 230 220 210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm 21.3 32.1 35.4 41.8 46.6 47.5 49.5 51.1 58.5 78.5 136.0 140.5 OAc H 122 5.3.3.4. COSY spectrum of 121 (CDCl3) ppm 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 ppm 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 OAc H 122 OAc H 121 OAc H 121

(21)

5.3.3.5. HSQC spectrum of 121 (CDCl3) ppm 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 ppm 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 OAc H 122 5.3.4.1. 1H NMR spectrum of 126b (CDCl3, 600 MHz) 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm 1.01 1.01 0.40 0.60 2.03 1.02 0.94 1.02 2.01 2.00 127b O Cl Cl Cl Cl Cl Cl OAc H 121 O Cl Cl Cl Cl Cl Cl 126b

(22)

5.3.4.2. 13C NMR spectrum of 126b (CDCl3, 150 MHz) 230 220 210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm -0.0 33 .6 40 .8 41 .0 41 .0 46 .2 46 .3 48 .0 55 .6 56 .1 56 .5 76 .8 77 .0 77 .2 80 .8 80 .9 1 04. 2 1 31. 0 1 31. 0 2 20. 1 127b O Cl Cl Cl Cl Cl Cl 5.3.4.3. DEPT spectrum of 126b (CDCl3) 230 220 210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm 33.6 40.8 41.0 41.0 46.2 46.3 48.0 55.6 56.1 56.5 127b O Cl Cl Cl Cl Cl Cl O Cl Cl Cl Cl Cl Cl 126b O Cl Cl Cl Cl Cl Cl 126b

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5.3.4.4. COSY spectrum of 126b (CDCl3) ppm 1.2 1.3 1.4 1.5 1.6 1.7 1.8 1.9 2.0 2.1 2.2 2.3 2.4 2.5 2.6 2.7 2.8 2.9 3.0 3.1 3.2 3.3 3.4 ppm 1.2 1.4 1.6 1.8 2.0 2.2 2.4 2.6 2.8 3.0 3.2 3.4 127b O Cl Cl Cl Cl Cl Cl 5.3.4.5. HSQC spectrum of 126b (CDCl3) ppm 1.0 1.5 2.0 2.5 3.0 3.5 4.0 4.5 5.0 5.5 6.0 6.5 7.0 7.5 ppm 240 220 200 180 160 140 120 100 80 60 40 20 0 127b O Cl Cl Cl Cl Cl Cl O Cl Cl Cl Cl Cl Cl 126b O Cl Cl Cl Cl Cl Cl 126b

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5.3.5.1. 1H NMR spectrum of 127 (CDCl3, 600 MHz) 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm 0.65 4.04 3.39 3.05 3.27 3.62 3.38 2.28 4.62 4.01 2.28 2.00 128 5.3.5.2. 13C NMR spectrum of 127 (CDCl3, 150 MHz) 210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm 25 .4 30 .8 43 .8 45 .0 46 .5 47 .3 47 .4 48 .7 53 .6 1 35. 8 128 127 127

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5.3.5.3. DEPT spectrum of 127 (CDCl3) 210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm 25.4 30.8 43.8 45.1 46.5 47.3 47.4 53.6 135.8 128 5.3.5.4. COSY spectrum of 127 (CDCl3) ppm 8 7 6 5 4 3 2 1 0 ppm -0.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 128 127 127

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5.3.5.5. HSQC spectrum of 127 (CDCl3) ppm -0.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 ppm 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 128 5.3.6.1. 1H NMR spectrum of 159 (CDCl3, 600 MHz) 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm 2.16 2.18 2.24 2.24 3.11 1.02 2.00 159 127 159

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5.3.6.2. 13C NMR spectrum of 159 (CDCl3, 150 MHz) 230 220 210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm 28 .3 31 .2 46 .2 47 .6 52 .7 57 .8 1 38. 8 159 5.3.6.3. DEPT spectrum of 159 (CDCl3) 230 220 210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm 25.6 28.3 31.2 46.2 47.6 52.7 57.8 77.2 138.8 159 159 159

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5.3.6.4. COSY spectrum of 159 (CDCl3) ppm 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 ppm -0.5 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 159 5.3.6.5. HSQC spectrum of 159 (CDCl3) ppm -0.5 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 ppm 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 159 159 159

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5.3.7.1. 1H NMR spectrum of 23 (CDCl3, 600 MHz) 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm 6.04 2.00 2.02 2.01 2.08 O O 24 5.3.7.2. 13C NMR spectrum of 23 (CDCl3, 150 MHz) 230 220 210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm -0.0 21 .3 38 .1 43 .2 44 .4 53 .5 76 .8 77 .0 77 .2 97 .8 1 21. 9 1 40. 2 2 12. 1 O O 24 O O 24 O O 24

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5.3.7.3. DEPT spectrum of 23 (CDCl3) 210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm 21.3 38.1 43.2 44.4 53.5 140.2 O O 24 5.3.7.4. COSY spectrum of 23 (CDCl3) ppm 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 ppm 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 O O 24 O O 24

(31)

5.3.7.5. HSQC spectrum of 23 (CDCl3) ppm -0.5 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 ppm 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 O O 24 5.3.8.1. 1H NMR spectrum of 132 (CDCl3, 600 MHz) 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm 0.34 6.75 1.95 0.97 1.02 1.00 1.99 1.00 4.05 O O O 133 O O 24 O O O 132

(32)

5.3.8.2. 13C NMR spectrum of 132 (CDCl3, 150 MHz) 230 220 210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm -0.0 21 .0 21 .0 35 .6 40 .8 41 .4 41 .7 43 .2 44 .8 49 .9 52 .1 64 .6 65 .7 76 .8 77 .0 77 .2 11 3. 9 11 9. 7 14 0. 4 21 5. 1 O O O 133 5.3.8.3. DEPT spectrum of 132 (CDCl3) 210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm 21.0 21.0 35.6 40.8 41.4 41.6 43.2 44.8 49.9 52.1 64.6 65.7 77.2 O O O 133 O O O 132 O O O 132

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5.3.8.4. COSY spectrum of 132 (CDCl3) ppm 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 ppm 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 O O O 133 5.3.8.5. HSQC spectrum of 132 (CDCl3) ppm 1.5 2.0 2.5 3.0 3.5 4.0 4.5 5.0 5.5 6.0 6.5 7.0 ppm 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 O O O 133 O O O 132 O O O 132

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5.3.8.6. NOESY spectrum of 132 (CDCl3, 600 MHz) ppm 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 ppm 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 O O O 133 5.3.9.1. 1H NMR spectrum of 133 (CDCl3, 600 MHz) 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm 0.30 0.13 6.18 1.04 2.08 1.07 2.09 1.04 1.07 1.06 1.07 1.07 2.08 1.00 O O HOH 134 O O H OH 133 O O O 132

(35)

5.3.9.2. 13C NMR spectrum of 133 (CDCl3, 150 MHz) 210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm -0.0 20 .7 20 .8 38 .4 39 .0 39 .2 39 .3 42 .7 43 .6 46 .4 46 .8 63 .0 65 .6 72 .7 76 .8 77 .0 77 .2 1 15. 7 1 17. 4 1 39. 1 O O H OH 134 5.3.9.3. DEPT spectrum of 133 (CDCl3) 210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm 20.7 20.8 38.4 39.0 39.2 39.3 42.6 43.6 46.4 46.8 63.0 65.6 72.7 77.2 O O H OH 134 O O H OH 133 O O H OH 133

(36)

5.3.9.4. COSY spectrum of 133 (CDCl3) ppm 1.5 2.0 2.5 3.0 3.5 4.0 4.5 5.0 5.5 ppm 1.5 2.0 2.5 3.0 3.5 4.0 4.5 5.0 5.5 O O H OH 134 5.3.9.5. HSQC spectrum of 133 (CDCl3) ppm 1.5 2.0 2.5 3.0 3.5 4.0 4.5 5.0 5.5 ppm 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 O O H OH 134 O O H OH 133 O O H OH 133

(37)

5.3.10.1. 1H NMR spectrum of 134a/134b (CDCl3, 600 MHz) 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm 6.96 4.88 5.10 1.17 4.63 5.49 0.81 2.27 135a 135b O HOH H OH O 5.3.10.2. 13C NMR spectrum of 134a/134b (CDCl3, 150 MHz) 230 220 210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm -0.0 20 .7 20 .8 20 .9 21 .0 36 .0 40 .5 40 .6 40 .7 41 .1 41 .1 42 .5 43 .9 44 .2 44 .8 45 .3 46 .4 49 .1 53 .3 53 .4 54 .6 72 .5 76 .8 77 .0 77 .2 81 .8 1 15. 8 1 18. 9 1 19. 3 1 40. 4 1 45. 9 2 19. 1 135a 135b O H OH H OH O O H OH H OH O 134a 134b O H OH H OH O 134a 134b

(38)

5.3.10.3. DEPT spectrum of 134a/134b (CDCl3) 210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm 20.7 20.8 20.9 21.0 36.0 40.5 40.6 40.7 41.0 41.1 42.5 43.8 44.1 44.8 45.3 46.4 49.0 53.3 53.3 54.6 72.5 81.8 135a 135b O H OH H OH O

5.3.10.4. COSY spectrum of 134a/134b (CDCl3)

ppm 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 ppm 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 135a 135b O H OH H OH O O H OH H OH O 134a 134b O H OH H OH O 134a 134b

(39)

5.3.10.5. HSQC spectrum of 134a/134b (CDCl3) ppm -0.5 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 ppm 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 135a 135b O H OH H OH O 5.3.11.1. 1H NMR spectrum of 151 (CDCl3, 600 MHz) 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 ppm 2.99 2.78 2.95 2.86 2.21 1.10 2.00 4.04 1.06 2.10 2.12 2.92 0.88 1.01 0.85 152a 152b O BrH Br O BrH Br O H OH H OH O 134a 134b O BrH Br O BrH Br 151a 151b

(40)

5.3.11.2. 13C NMR spectrum of 151 (CDCl3, 150 MHz) 210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm 19 .6 19 .8 19 .9 19 .9 31 .7 34 .2 34 .4 37 .4 41 .2 44 .3 45 .3 45 .4 45 .4 47 .6 51 .6 52 .4 52 .8 52 .8 53 .5 53 .6 54 .7 57 .3 57 .6 57 .6 87 .0 88 .4 2 13. 4 2 13. 4 152a 152b O BrH Br O BrH Br 5.3.11.3. DEPT spectrum of 151 (CDCl3) 210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm 19.6 19.8 19.9 20.0 31.7 34.2 34.4 37.4 41.2 44.3 45.3 45.4 45.4 47.6 51.6 52.4 52.8 52.8 53.6 54.7 57.3 57.6 57.6 77.2 152a 152b O Br H Br O BrH Br O BrH Br O BrH Br 151a 151b O BrH Br O BrH Br 151a 151b

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5.3.11.4. COSY spectrum of 151 (CDCl3) ppm 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 ppm 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 152a 152b O BrH Br O BrH Br 5.3.11.5. HSQC spectrum of 151 (CDCl3) ppm 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 ppm 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 152a 152b O BrH Br O BrH Br O BrH Br O BrH Br 151a 151b O BrH Br O BrH Br 151a 151b

(42)

5.3.12.1. 1H NMR spectrum of 3 (CDCl3, 600 MHz) 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm 2.01 1.96 1.99 2.03 2.00 1.92 O O 3 5.3.12.2. 13C NMR spectrum of 3 (CDCl3, 150 MHz) 230 220 210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm 32 .7 34 .6 36 .7 36 .8 37 .0 39 .1 39 .2 39 .4 39 .5 39 .6 39 .8 39 .9 40 .0 46 .2 47 .4 47 .9 48 .9 1 09. 9 1 40. 1 1 40. 3 2 11. 9 O O 3 O O 3 O O 3

(43)

5.3.12.3. DEPT spectrum of 3 (CDCl3) 230 220 210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm 32.7 34.6 36.7 36.8 37.0 39.3 39.5 39.6 39.8 39.9 40.0 46.2 47.4 47.9 48.9 140.1 140.3 O O 3 5.3.12.4. COSY spectrum of 3 (CDCl3) ppm 1.5 2.0 2.5 3.0 3.5 4.0 4.5 5.0 5.5 6.0 6.5 7.0 ppm 1.5 2.0 2.5 3.0 3.5 4.0 4.5 5.0 5.5 6.0 6.5 7.0 O O 3 O O 3 O O 3

(44)

5.3. 12.5. HSQC spectrum of 3 (CDCl3) ppm 1.5 2.0 2.5 3.0 3.5 4.0 4.5 5.0 5.5 6.0 6.5 7.0 ppm 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 O O 3 5.3.13.1. 1H NMR spectrum of 175 (CDCl3, 600 MHz) 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 ppm 2.36 2.10 2.74 2.53 2.15 2.61 1.94 2.00 175 O O 3 175

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5.3.13.2. 13C NMR spectrum of 175 (CDCl3, 150 MHz) 210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm 27 .1 36 .1 36 .7 37 .3 41 .0 41 .1 1 40. 5 175 5.3.13.3. DEPT spectrum of 175 (CDCl3) 210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm 27.0 36.0 36.7 37.3 41.0 41.1 140.5 175 175 175

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5.3.13.4. COSY spectrum of 175 (CDCl3) ppm 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 ppm 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 175 5.3.13.5. HSQC spectrum of 175 (CDCl3) ppm 1.5 2.0 2.5 3.0 3.5 4.0 4.5 5.0 5.5 6.0 6.5 ppm 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 175 175 175

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5.3.15. Selected 1H NMR signals of the 159/Grubbs-II reaction mixture at different time intervals at

40oC (CDCl3, 600 MHz)

(a) Olefinic proton of 159 at H = 6.06 ppm

t = 10 mi n t = 20 mi n t = 30 mi n t = 40 mi n t = 50 mi n t = 60 mi n t = 70 mi n t = 80 mi n t = 80 mi n t = 90 mi n t = 100 mi n t = 110 mi n t = 120 mi n t = 130 mi n t = 140 mi n t = 150 mi n t = 150 mi n t = 160 mi n t = 170 mi n t = 180 mi n t = 190 mi n t = 200 mi n

(b) Carbene proton of Grubbs-II at H = 19.18 ppm

t = 10 mi n t = 20 mi n t = 30 mi n t = 40 mi n t = 50 mi n t = 60 mi n t = 70 mi n t = 80 mi n t = 80 mi n t = 90 mi n t = 100 mi n t = 110 mi n t = 120 mi n t = 130 mi n t = 140 mi n t = 150 mi n t = 150 mi n t = 160 mi n t = 170 mi n t = 180 mi n t = 190 mi n t = 200 mi n

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5.3.16. Selected 1H NMR signals of the 1/Grubbs-II reaction mixture at different time intervals at

40oC (CDCl3, 600 MHz)

(a) Olefinic proton of 1 at H = 6.00 ppm

t = 10 mi n t = 20 mi n t = 30 mi n t = 40 mi n t = 50 mi n t = 60 mi n t = 70 mi n t = 80 mi n t = 80 mi n t = 90 m in t = 100 m in t = 110 m in t = 120 m in

(b) Carbene proton of Grubbs-II at H = 19.19 ppm

t = 10 min t = 20 min t = 30 min t = 40 min t = 50 min t = 60 min t = 70 min t = 80 min t = 80 min t = 90 min t = 10 0 min t = 11 0 min t = 12 0 min

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