APPENDIX 4

APPENDIX 4

Spectra Relevant to Chapter 2:

Acyl-Amination of Arenes via Aryne Formation

Appendix 4–Spectra Relevant to Chapter 2 175

Me Me

N H

OO Me

Me S2 1 H NMR (400 MHz, CDCl3) of compound xxFigure A4.11H NMR (400 MHz, CDCl3) of compound 109

Infrared spectrum (Thin Film, NaCl) of compound xx

13C NMR (101 MHz, CDCl3) of compound xx Infrared spectrum (Thin Film, NaCl) of compound xx

13C NMR (101 MHz, CDCl3) of compound xx

Figure A4.2 Infrared spectrum (Thin Film, NaCl) of compound 109

Figure A4.3 ¹³C NMR (101 MHz, CDCl3) of compound 109

Appendix 4–Spectra Relevant to Chapter 2 177

Ph

H N

O

OMe O S5

1 H NMR (400 MHz, CDCl3) of compound xxFigure A4.41H NMR (400 MHz, CDCl3) of compound 112

13C NMR (101 MHz, CDCl3) of compound xx

13C NMR (101 MHz, CDCl3) of compound xx

Figure A4.5 Infrared spectrum (Thin Film, NaCl) of compound 112

Figure A4.6 ¹³C NMR (101 MHz, CDCl3) of compound 112

Appendix 4–Spectra Relevant to Chapter 2 179

Me Me

O HN O

MeMe 13c 1 H NMR (400 MHz, CDCl3) of compound xxFigure A4.71 H NMR (400 MHz, CDCl3) of compound 104c

13C NMR (101 MHz, CDCl3) of compound xx Infrared spectrum (Thin Film, NaCl) of compound xx

13C NMR (101 MHz, CDCl3) of compound xx Infrared spectrum (Thin Film, NaCl) of compound xx Figure A4.8 Infrared spectrum (Thin Film, NaCl) of compound 104c

Figure A4.9 ¹³C NMR (101 MHz, CDCl3) of compound 104c

Appendix 4–Spectra Relevant to Chapter 2 181

Me MeOMe HN OMe 13d 1 H NMR (400 MHz, CDCl3) of compound xxFigure A4.101 H NMR (400 MHz, CDCl3) of compound 104d

13C NMR (101 MHz, CDCl3) of compound xx Infrared spectrum (Thin Film, NaCl) of compound xx

13C NMR (101 MHz, CDCl3) of compound xx Infrared spectrum (Thin Film, NaCl) of compound xx Figure A4.11 Infrared spectrum (Thin Film, NaCl) of compound 104d

Figure A4.12 ¹³C NMR (101 MHz, CDCl3) of compound 104d

Appendix 4–Spectra Relevant to Chapter 2 183

OMe

O NH OBn 13e 1 H NMR (400 MHz, CDCl3) of compound xxFigure A4.131H NMR (400 MHz, CDCl3) of compound 104e

13C NMR (101 MHz, CDCl3) of compound xx

Infrared spectrum (Thin Film, NaCl) of compound xx

13C NMR (101 MHz, CDCl3) of compound xx

Infrared spectrum (Thin Film, NaCl) of compound xx

Figure A4.14 Infrared spectrum (Thin Film, NaCl) of compound 104e

Figure A4.15 ¹³C NMR (101 MHz, CDCl3) of compound 104e

Appendix 4–Spectra Relevant to Chapter 2 185

MeO

NHMe

Me

O Me 15a 1 H NMR (400 MHz, CDCl3) of compound xx Figure A4.161H NMR (400 MHz, CDCl3) of compound 106a

13C NMR (101 MHz, CDCl3) of compound xx Infrared spectrum (Thin Film, NaCl) of compound xx

13C NMR (101 MHz, CDCl3) of compound xx Infrared spectrum (Thin Film, NaCl) of compound xx

Figure A4.17 Infrared spectrum (Thin Film, NaCl) of compound 106a

Figure A4.18 ¹³C NMR (101 MHz, CDCl3) of compound 106a

Appendix 4–Spectra Relevant to Chapter 2 187

Me

O NH OMe 15b 1 H NMR (400 MHz, CDCl3) of compound xxFigure A4.191H NMR (400 MHz, CDCl3) of compound 106b

13C NMR (101 MHz, CDCl3) of compound xx Infrared spectrum (Thin Film, NaCl) of compound xx

13C NMR (101 MHz, CDCl3) of compound xx Infrared spectrum (Thin Film, NaCl) of compound xx

Figure A4.20 Infrared spectrum (Thin Film, NaCl) of compound 106b

Figure A4.21 ¹³C NMR (101 MHz, CDCl3) of compound 106b

Appendix 4–Spectra Relevant to Chapter 2 189

Me

O OO NH OMe 15c 1 H NMR (400 MHz, CDCl3) of compound xxFigure A4.221 H NMR (400 MHz, CDCl3) of compound 106c

13C NMR (101 MHz, CDCl3) of compound xx Infrared spectrum (Thin Film, NaCl) of compound xx

13C NMR (101 MHz, CDCl3) of compound xx Infrared spectrum (Thin Film, NaCl) of compound xx

Figure A4.23 Infrared spectrum (Thin Film, NaCl) of compound 106c

Figure A4.24 ¹³C NMR (101 MHz, CDCl3) of compound 106c

Appendix 4–Spectra Relevant to Chapter 2 191

OMe Me

O NH OMe 15d 1 H NMR (500 MHz, CDCl3) of compound xxFigure A4.251 H NMR (500 MHz, CDCl3) of compound 106d

Infrared spectrum (Thin Film, NaCl) of compound xx

13C NMR (101 MHz, CDCl3) of compound xx Infrared spectrum (Thin Film, NaCl) of compound xx

13C NMR (101 MHz, CDCl3) of compound xx

Figure A4.26 Infrared spectrum (Thin Film, NaCl) of compound 106d

Figure A4.27 ¹³C NMR (126 MHz, CDCl3) of compound 106d

Appendix 4–Spectra Relevant to Chapter 2 193

N H

Me

OOMe 16c 1 H NMR (400 MHz, CDCl3) of compound xxFigure A4.281H NMR (400 MHz, CDCl3) of compound 107c

Infrared spectrum (Thin Film, NaCl) of compound xx

13C NMR (101 MHz, CDCl3) of compound xx Infrared spectrum (Thin Film, NaCl) of compound xx

13C NMR (101 MHz, CDCl3) of compound xx

Figure A4.29 Infrared spectrum (Thin Film, NaCl) of compound 107c

Figure A4.30 ¹³C NMR (101 MHz, CDCl3) of compound 107c

Appendix 4–Spectra Relevant to Chapter 2 195

1 H NMR (400 MHz, CDCl3) of compound xx

N H

Me

O 16a Figure A4.311H NMR (400 MHz, CDCl3) of compound 107a

1 H NMR (400 MHz, CDCl3) of compound xx

N H

Me

OOMe MeO 16b Figure A4.321 H NMR (400 MHz, CDCl3) of compound 107b