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1 Supplemental material: REGIOSPECIFIC SYNTHESIS OF DIMETHYLPHENANTHRENES Thomas Böhme, Marianne Lorentzen and Kåre B. Jørgensen* Faculty of Science and Technology, University of Stavanger, N-4036 Stavanger, Norway Contents: Page S2: 1 H-NMR of 4a (2,3-dimethylphenanthrene) Page S3: 1 H-NMR of 4b (2,7-dimethylphenanthrene) Page S4: 1 H-NMR of 4c (2,6-dimethylphenanthrene) (not recrystallized) Page S5: 1 H-NMR of 4d (1,7-dimethylphenanthrene) Page S6: GC-FID of blank Page S7: GC-FID of 4a (2,3-dimethylphenanthrene) Page S9: GC-FID of 4b (2,7-dimethylphenanthrene) Page S11: GC-FID of 4c (2,6-dimethylphenanthrene) (not recrystallized) Page S13: GC-FID of 4d (1,7-dimethylphenanthrene) 1 H-NMR was recorded at a Bruker 400 MHz instrument. GC-FID were performed on a Agilent 6890N GC-FID with a 30m 0.25mm Agilent DB- 225MS column with 21 cm/s He-flow. The sample was dissolved in acetone and injected as 1 µl split(10:1) injection at 250 C. The temperature program was 80 C/1 min, 10 C/min to 200 C, 3 C/min to 230 C, and 230 C/11 min. [ S1 ]
2 4a CDCl ppm Current Data Parameters NAME 4a EXPNO 1 PROCNO 1 F2 - Acquisition Parameters Date_ Time INSTRUM spect PROBHD 5 mm PABBO BB/ PULPROG zg30 TD SOLVENT CDCl3 NS 16 DS 2 SWH Hz FIDRES Hz AQ sec RG DW usec DE 6.50 usec TE K D1 1. sec TD0 1 ======== CHANNEL f1 ======== SFO MHz NUC1 1H P usec PLW W F2 - Processing parameters SI SF MHz WDW EM SSB 0 LB 0.30 Hz GB 0 PC [ S2 ]
3 ppm Current Data Parameters NAME 4b EXPNO 1 PROCNO 1 F2 - Acquisition Parameters Date_ Time INSTRUM spect PROBHD 5 mm PABBO BB/ PULPROG zg30 TD SOLVENT CDCl3 NS 16 DS 2 SWH Hz FIDRES Hz AQ sec RG DW usec DE 6.50 usec TE K D1 1. sec TD0 1 ======== CHANNEL f1 ======== SFO MHz NUC1 1H P usec PLW W F2 - Processing parameters SI SF MHz WDW EM SSB 0 LB 0.30 Hz GB 0 PC b CDCl3 [ S3 ]
4 4c CDCl ppm Current Data Parameters NAME 4c EXPNO 1 PROCNO 1 F2 - Acquisition Parameters Date_ Time INSTRUM spect PROBHD 5 mm PABBO BB/ PULPROG zg30 TD SOLVENT CDCl3 NS 16 DS 2 SWH Hz FIDRES Hz AQ sec RG DW usec DE 6.50 usec TE K D1 1. sec TD0 1 ======== CHANNEL f1 ======== SFO MHz NUC1 1H P usec PLW W F2 - Processing parameters SI SF MHz WDW EM SSB 0 LB 0.30 Hz GB 0 PC [ S4 ]
5 d CDCl3 Water ppm Current Data Parameters NAME K-154 Thomas 7D recryst EXPNO 1 PROCNO 1 F2 - Acquisition Parameters Date_ Time INSTRUM spect PROBHD 5 mm PABBO BB/ PULPROG zg30 TD SOLVENT CDCl3 NS 16 DS 2 SWH Hz FIDRES Hz AQ sec RG DW usec DE 6.50 usec TE K D1 1. sec TD0 1 ======== CHANNEL f1 ======== SFO MHz NUC1 1H P usec PLW W F2 - Processing parameters SI SF MHz WDW EM SSB 0 LB 0.30 Hz GB 0 PC 1.00 [ S5 ]
6 File :C:\MassHunter\GCMS\1\data\Kåre\ \blank.D Operator : Acquired : 29 Feb :04 using Acq Kaare_Phenanthrene.M Instrument : GCMS Sample Name: Misc Info : Vial Number: 29 Response_ Signal: blank.d\fid1a.ch Time [ S6 ]
7 Data File : 4a.D Acq On : 29 Feb :16 ALS Vial : 30 Sample Multiplier: 1 Signal : FID1A.ch peak R.T. Start End PK peak peak peak % of # min min min TY height area % max. total BB % 0.223% BB % 0.467% BB % % Sum of corrected areas: [ S7 ] FAME extrac... 9 dec FID.M Tue Mar 01 10:26: GC Page: 1
8 Data File : 4a.D Acq On : 29 Feb :16 ALS Vial : 30 Sample Multiplier: 1 Response_ Signal: 4a.D\FID1A.ch View Mode: Integration Time [ S8 ] FAME extrac... 9 dec FID.M Tue Mar 01 10:26: GC Page: 2
9 Data File : 4b.D Acq On : 29 Feb :02 ALS Vial : 31 Sample Multiplier: 1 Signal : FID1A.ch peak R.T. Start End PK peak peak peak % of # min min min TY height area % max. total BB % 0.701% BB % % BB % % BB % 1.299% Sum of corrected areas: [ S9 ] FAME extrac... 9 dec FID.M Tue Mar 01 10:28: GC Page: 1
10 Data File : 4b.D Acq On : 29 Feb :02 ALS Vial : 31 Sample Multiplier: 1 Response_ Signal: 4b.D\FID1A.ch View Mode: Integration Time [ S ] FAME extrac... 9 dec FID.M Tue Mar 01 10:28: GC Page: 2
11 Data File : 4c.D Acq On : 29 Feb :40 ALS Vial : 32 Sample Multiplier: 1 Signal : FID1A.ch peak R.T. Start End PK peak peak peak % of # min min min TY height area % max. total BB % 1.725% BB % 3.951% BB % % BB % 0.933% BB % % BB % 4.360% Sum of corrected areas: [ S11 ] FAME extrac... 9 dec FID.M Tue Mar 01 10:29: GC Page: 1
12 Data File : 4c.D Acq On : 29 Feb :40 ALS Vial : 32 Sample Multiplier: 1 Response_ Signal: 4c.D\FID1A.ch View Mode: Integration Time [ S ] FAME extrac... 9 dec FID.M Tue Mar 01 10:29: GC Page: 2
13 Data File : 4d.D Acq On : 29 Feb :20 ALS Vial : 33 Sample Multiplier: 1 Signal : FID1A.ch peak R.T. Start End PK peak peak peak % of # min min min TY height area % max. total BB % 2.770% BB % 0.545% BB % % Sum of corrected areas: [ S13 ] FAME extrac... 9 dec FID.M Tue Mar 01 10:30: GC Page: 1
14 Data File : 4d.D Acq On : 29 Feb :20 ALS Vial : 33 Sample Multiplier: 1 Response_ Signal: 4d.D\FID1A.ch View Mode: Integration Time [ S ] FAME extrac... 9 dec FID.M Tue Mar 01 10:30: GC Page: 2
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