Supporting Information
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- Ὑμέναιος Λόντος
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1 Supporting Information Direct Olefination of Alcohols with Sulfones by Using Heterogeneous Platinum Catalysts S. M. A. Hakim Siddiki, [a] Abeda Sultana Touchy, [b] Kenichi Kon, [b] [a, b] and Ken-ichi Shimizu* chem_ _sm_miscellaneous_information.pdf
2 Supporting Information Direct Olefination of Alcohols with Sulfones by Heterogeneous Platinum Catalysts S. M. A. Hakim Siddiki, a Abeda Sultana Touchy, b Kenichi Kon, b Ken-ichi Shimizu* a,b a Elements Strategy Initiative for Catalysts and Batteries, Kyoto University, Katsura, Kyoto , Japan b Institute for Catalysis, Hokkaido University, N-21, W-10, Sapporo , Japan *Corresponding author Ken-ichi Shimizu Institute for Catalysis, Hokkaido University, N-21, W-10, Sapporo , Japan kshimizu@cat.hokudai.ac.jp, Fax: NMR and GC/MS analysis 1 H and 13 C NMR spectra for olefins of Table-4 and Table-5 were assigned and reproduced to the corresponding literature. 1 H and 13 C NMR spectra were recorded using at ambient temperature on JEOL-ECX 600 operating at and MHz, respectively with tetramethylsilane as an internal standard. All chemical shifts (δ) are reported in ppm and coupling constants (J) in Hz. All chemical shifts are reported relative to tetramethylsilane and d-solvent peaks ppm chloroform. Abbreviations used in the NMR experiments: s, singlet; d, doublet; t, triplet; q, quartet; m, multiplet. GC-MS spectra was taken by SHIMADZU QP2010. Vinyl-benzene: GC-MS m/e Methyl-4-vinyl-benzene : [1] 1 H NMR ( MHz, CDCl 3, TMS): δ 7.28 (d, J = 8.22 Hz, 2H), 7.10 (d, J = 7.62 Hz, 2H), 6.80 (dd, J = 17.82, Hz, 1H), 5.68 (d, J = Hz, 1H), 5.16 (d, J = Hz, 1H), 2.33 (s, 3H); 13 C NMR ( MHz, CDCl 3 ) δ , , , (C 2), (C 2), , 21.17; GC-MS m/e
3 1-Methoxy-4-vinyl-benzene : [1] MeO 1 H NMR ( MHz, CDCl 3, TMS): δ 7.33 (d, J = 8.94 Hz, 2H), 7.10 (d, J = 8.94 Hz, 2H), 6.64 (dd, J = 17.52, Hz, 1H), 5.61 (d, J = Hz, 1H), 5.12 (d, J = Hz, 1H), 3.78 (s, 3H); 13 C NMR ( MHz, CDCl 3 ) δ , , , , (C 2), , , 55.20; GC-MS m/e (tert-Butyl)-4-vinyl-benzene : [2] 1 H NMR ( MHz, CDCl 3, TMS): δ 7.34 (s like, 4H), 6.68 (dd, J = 17.88, Hz, 1H), 5.70 (d, J = Hz, 1H), 5.18 (d, J = Hz, 1H), 1.31 (s, 9H); 13 C NMR ( MHz, CDCl 3 ) δ , , , , , , , , 34.54, (C 3); GC-MS m/e Fluoro-4-vinyl-benzene: GC-MS m/e F 1-Chloro-4-vinyl-benzene: GC-MS m/e Cl 1-Trifluoromethyl-4-vinyl-benzene: GC-MS m/e F 3 C 4-Vinyl-biphenyl : [1] Ph 1 H NMR ( MHz, CDCl 3, TMS): δ ( m, 2H), (m, 2H), (m, 2H), (m, 2H), (m, 1H), 6.74 (dd, J = 17.16, Hz, 1H), 5.78(d, J = Hz, 1H), 5.25 (d, J = Hz, 1H); 13 C NMR ( MHz, CDCl 3 ) δ , , , , (C 2), (C 2), , (C 2), (C 2), ; GC-MS m/e
4 1,2-Dimethoxy-4-vinyl-benzene : [1] MeO OMe 1 H NMR ( MHz, CDCl 3, TMS): δ ( m, 2H), 6.80 (d, J = 8.22 Hz, 1H), 6.64 (dd, J = 17.82, Hz, 1H), 5.60 (d, J = Hz, 1H), 5.14 (d, J = Hz, 1H), 3.89 (s, 3H), 3.86 (s, 3H); 13 C NMR ( MHz, CDCl 3 ) δ , , , , , , , , 55.75, 55.64; GC-MS m/e Vinylnapthalene : [1] 1 H NMR ( MHz, CDCl 3, TMS): δ (m, 3H), 7.66 (s, 1H), 7.57 (dd, J = 8.94, 2.04 Hz, 1H), (m, 2H), 6.80 (dd, J = 17.62, Hz, 1H), 5.78(d, J = Hz, 1H), 5.25 (d, J = Hz, 1H); 13 C NMR ( MHz, CDCl 3 ) δ , , , , , , , , , , , ; GC-MS m/e Vinylnapthalene : [1] 1 H NMR ( MHz, CDCl 3, TMS): δ 8.07 (d, J = 7.56 Hz, 1H), 7.80 (d, J = 8.22 Hz, 1H), 7.73 (d, J = 8.22 Hz, 1H), 7.58 (d, J = 7.56 Hz, 1H), (m, 4H), 5.75 (dd, J = 17.62, 1.38 Hz, 1H), 5.43 (dd, J = 10.68, 1.38 Hz, 1H); 13 C NMR ( MHz, CDCl 3 ) δ , , , , , , , , , , , ; GC-MS m/e Vinyl-furan: GC-MS m/e O 2-Vinyl-thiophene: GC-MS m/e S 3
5 2-Vinylpyridine : [3] N 1 H NMR ( MHz, CDCl 3, TMS): δ 8.57 (d like s, 1H), 7.64 (t, J = 7.56 Hz, 1H), 7.34 (d, J = 7.56 Hz, 1H), 7.15 (m, 1H), 6.82 (dd, J = 17.88, Hz, 1H), 6.20 (d, J = Hz, 1H), 5.48 (d, J = Hz, 1H); 13 C NMR ( MHz, CDCl 3 ) δ , , , , , , ; GC-MS m/e Vinyl-benzo[1,3]dioxole: [4] O O 1 H NMR ( MHz, CDCl 3, TMS): δ 6.95 (s, 1H), 6.80 (dd, J = 8.37, 1.38 Hz, 1H), 6.75 (d, J = 7.65 Hz, 1H), 6.60 (dd, J = 17.24, Hz, 1H), 5.94 (s, 2H), 5.56 (d, J = Hz, 1H), 5.12 (d, J = Hz, 1H); 13 C NMR ( MHz, CDCl 3 ) δ , , , , , , , , ; GC-MS m/e Non-1-ene: GC-MS m/e n-c 7 H 15 Vinyl-cyclohexane: GC-MS m/e Methyl-penta-1,3-diene:GC-MS m/e Buta-1,3-dienyl-benzene : [5] 1 H NMR ( MHz, CDCl 3, TMS): δ 7.39 (d, J = 8.22 Hz, 2H), ( m, 2H), (m, 1H), 6.80 (dd, J = 18.48, Hz, 1H), 6.51(dd, J = 17.16, 9.60 Hz, 2H), 5.32 (d, J = Hz, 1H), 5.16 (d, J = 9.60 Hz, 1H); 13 C NMR ( MHz, CDCl 3 ) δ , , , , (C 2), , (C 2), ; GC-MS m/e
6 Isopropenyl-benzene : [6] 1 H NMR ( MHz, CDCl 3, TMS): δ (m, 2H), (m, 2H)), (m, 1H), 5.36 (s, 1H), 5.08 (s, 1H), 2.15 (s, 3H); 13 C NMR ( MHz, CDCl 3 ) δ , , (C 2), , (C 2), , 21.80; GC-MS m/e Isopropenyl-4-methyl-benzene : [6] 1 H NMR ( MHz, CDCl 3, TMS): δ 7.37 (d, J = 8.22 Hz, 2H), 7.13 (d, J = 8.22 Hz, 2H), 5.33 (s, 1H), 5.02 (s, 1H), 2.33 (s, 3H), 2.13 (s, 3H); 13 C NMR ( MHz, CDCl 3 ) δ , , , (C 2), (C 2), , 21.83, 21.04; GC-MS m/e Isopropenyl-4-methoxy-benzene: [7] MeO 1 H NMR ( MHz, CDCl 3, TMS): δ 7.41 (d, J = 8.61 Hz, 2H), 6.85 (d, J = 8.61 Hz, 2H), 5.28 (s, 1H), 4.98 (s, 1H), 3.80 (s, 3H), 2.12 (s, 3H); 13 C NMR ( MHz, CDCl 3 ) δ , , , (C 2), (C 2), , 55.24, 21.88; GC-MS m/e Isopropenyl-naphthalene : [8] 1 H NMR ( MHz, CDCl 3, TMS): δ (m, 4H), 7.66 (dd, J = 8.64, 2.04 Hz, 1H), (m, 2H), 5.53 (s, 1H), 5.19 (s, 1H), 2.26 (s, 3H); 13 C NMR ( MHz, CDCl 3 ) δ , , , , , , , , , , , , 21.86; GC-MS m/e ,1-Diphenyl-ethene : [9] 5
7 1 H NMR ( MHz, CDCl 3, TMS): δ (m, 10H), 5.45 (s, 2H); 13 C NMR ( MHz, CDCl 3 ) δ , (C 2), (C 4), (C 4), (C 2), ; GC-MS m/e Propenyl-benzene: GC-MS m/e Methyl-4-propenyl-benzene: [1] 1 H NMR ( MHz, CDCl 3, TMS): δ 7.21 (d, J = 8.22 Hz, 2H), 7.08 (d, J = 7.56 Hz, 2H), 6.35 (d, J = Hz, 1H), (m, 1H), 2.31 (s, 3H), 1.86 (d, J = 6.90 Hz, 3H); 13 C NMR ( MHz, CDCl 3 ): δ , , , (C 2), (C 2), , 21.10, 18.44; GC-MS m/e Methoxy-4-propenyl-benzene: [1] MeO 1 H NMR ( MHz, CDCl 3, TMS): δ 7.24 (d, J = 8.28 Hz, 2H), 6.81 (d, J = 8.28 Hz, 2H), 6.32 (d, J = Hz, 1H), (m, 1H), 3.77 (s, 3H), 1.84 (d, J = 6.90 Hz, 3H); 13 C NMR ( MHz, CDCl 3 ): δ , , , (C 2), , (C 2), 55.22, 18.40; GC-MS m/e tert-Butyl-4-propenyl-benzene: [10] 1 H NMR ( MHz, CDCl 3, TMS): δ 7.31 (d like, 2H), 7.27 (d like, 2H), 6.37 (d, J = Hz, 1H), (m, 1H), 1.86 (d, J = 4.80 Hz, 3H), 1.30 (s, 9H); 13 C NMR ( MHz, CDCl 3 ): δ , , , (C 2), (C 2), , 34.45, (C 3), 18.48; GC-MS m/e Chloro-4-propenyl-benzene:GC-MS m/e Cl 6
8 4-Propenyl-biphenyl: [11] Ph 1 H NMR ( MHz, CDCl 3, TMS): δ 7.56 (d, J = 6.90 Hz, 2H), 7.50 (d, J = 8.28 Hz, 2H), (m, 4H), (m, 1H), 6.41 (d, J = Hz, 1H), (m, 1H), 1.87 (d, J = 6.84 Hz, 3H); 13 C NMR ( MHz, CDCl 3 ): δ , , , , (C 2), (C 2), , (C 2), (C 2), , 18.54; GC-MS m/e ,2-Dimethoxy-4-propenyl-benzene:GC-MS m/e MeO OMe 2-Propenyl-naphthalene: [1] 1 H NMR ( MHz, CDCl 3, TMS): δ (m, 3H), 7.63 (s, 1H), 7.54 (dd, J = 8.64, 2.04 Hz, 1H), (m, 2H), 6.54 (d, J = Hz, 1H), (m, 1H), 1.91 (d, J = 4.80 Hz, 3H); 13 C NMR ( MHz, CDCl 3 ): δ, , , , , , , , , , , , , 18.61; GC-MS m/e Propenyl-thiophene: [12] S 1 H NMR ( MHz, CDCl 3, TMS): δ 7.06 (d, J = 5.46 Hz, 1H), 6.91 (t, J = 4.80 Hz, 1H), 6.84 (d, J = 2.76 Hz, 1H), 6.51 (d, J = Hz, 1H), (m, 1H), 1.84 (d, J = 6.90 Hz, 3H); 13 C NMR ( MHz, CDCl 3 ): δ , , , , , , ; GC-MS m/e Propenyl-pyridine: [13] N 1 H NMR ( MHz, CDCl 3, TMS): δ 8.55 (s, 1H), 8.42 (s, 1H), 7.64 (d, J = 7.56 Hz, 1H), (m, 1H), 6.38 (d, J = Hz, 1H), (m, 1H), 1.91 (d, J = 7.56 Hz, 3H); 13 C NMR ( MHz, CDCl 3 ): δ , , , , , , , ; 7
9 GC-MS m/e Propenyl-benzo[1,3]dioxole: [14] O O 1 H NMR ( MHz, CDCl 3, TMS): δ 6.87 (s, 1H), 6.72 (s, 2H), 6.29 (d, J = Hz, 1H), (m, 1H), 5.91 (s, 2H), 1.84 (d, J = 6.18 Hz, 3H), 13 C NMR ( MHz, CDCl 3 ): δ , , , , , , , , , 18.30; GC-MS m/e Penta-1,3-dienyl-benzene: [15] 1 H NMR ( MHz, CDCl 3, TMS): δ 7.40 (d, J = 6.90 Hz, 2H), (m, 2H), (m, 1H), (m, 1H), 6.46 (d, J = Hz, 1H), (m, 1H), (m, 1H), 1.86 (d, J = 6.18 Hz, 3H); 13 C NMR ( MHz, CDCl 3 ): δ , , , , , (C 2), , (C 2), 18.32; GC-MS m/e (E)-1,2-Diphenylethene [16] Ph 1 H NMR ( MHz, CDCl 3, TMS): δ 7.50 (d, J = 7.56 Hz, 4H), 7.34 (t, J = 7.62 Hz, 4H), 7.24 (t, J = 7.56 Hz, 2H), 7.09 (s, 2H); 13 C NMR ( MHz, CDCl 3 ): δ (C 2), (C 4), (C 2), , (C 4), ; GC-MS m/e Methyl-4-styryl-benzene: [1] Ph 1 H NMR ( MHz, CDCl 3, TMS): δ 7.49 (d, J = 7.56 Hz, 2H), 7.40 (d, J = 8.28 Hz, 2H), 7.34 (t, J = 7.56 Hz, 2H), 7.23 (t, J = 7.56 Hz, 1H), 7.16 (d, J = 8.22 Hz, 2H), 7.06 (d, J = 4.80 Hz, 2H), 2.35 (s, 3H); 13 C NMR ( MHz, CDCl 3 ): δ , , , (C 2), (C 2), , , , (C 2), (C 2), 21.24; GC-MS m/e
10 1-Methoxy-4-styryl-benzene: [1] Ph MeO 1 H NMR ( MHz, CDCl 3, TMS): δ 7.48 (d, J = 7.56 Hz, 2H), 7.44 (d, J = 8.22 Hz, 2H), 7.33 (t, J = 7.56 Hz, 2H), 7.22 (t, J = 7.56 Hz, 1H), 7.06 (d, J = Hz, 1H), 6.97 (d, J = Hz, 1H), 6.89 (d, J = 8.22 Hz, 2H), 3.82 (s, 3H); 13 C NMR ( MHz, CDCl 3 ): δ , , , (C 2), , (C 2), , , (C 2), (C 2), 55.32; GC-MS m/e tert-Butyl-4-styryl-benzene: [16] Ph 1 H NMR ( MHz, CDCl 3, TMS): δ 7.49 (d, J = 7.56 Hz, 2H), 7.45 (d, J = 8.22 Hz, 2H), 7.36 (d, J = 8.22 Hz, 2H), 7.34 (t, J = 7.56 Hz, 2H), 7.23 (t, J = 7.56 Hz, 1H), 7.08 (d, J = 5.52 Hz, 2H), 1.31 (s, 9H); 13 C NMR ( MHz, CDCl 3 ): δ , , , (C 2), , , , (C 2), (C 2), (C 2), 34.60, 31.27; GC-MS m/e Fluoro-4-styryl-benzene: [16] Ph F 1 H NMR ( MHz, CDCl 3, TMS): δ (m, 4H), 7.35 (t, J = 7.56 Hz, 2H), 7.26 (t, J = 7.56 Hz, 1H), (m, 4H); 13 C NMR ( MHz, CDCl 3 ): δ (d, J = Hz, 4-F-C ), , , , , (d, J = 8.06 Hz, meta to 4-F, C 2 ), , , , (d, J = 8.06 Hz, ortho to 4-F, C 2 ); GC-MS m/e Chloro-4-styryl-benzene: [1] Ph Cl 1 H NMR ( MHz, CDCl 3, TMS): δ 7.49 (d, J = 7.56 Hz, 2H), 7.42 (d, J = 8.22 Hz, 2H), 7.35 (t, J = 7.56 Hz, 2H), 7.31 (d, J = 8.22 Hz, 2H), 7.26 (t, J = 7.56 Hz, 1H), 7.06 (d, J = 5.46 Hz, 2H); 13 C NMR ( MHz, CDCl 3 ): δ , , , , (C 2), (C 2), , (C 2), , (C 2); GC-MS m/e
11 4-Styryl-biphenyl: [1] Ph Ph 1 H NMR ( MHz, CDCl 3, TMS): δ (m, 3H), 7.45 (d, J = 8.22Hz, 2H), 7.41 (t, J = 7.56 Hz, 2H), (m, 4H), 7.24 (t, J = 7.56 Hz, 2H), 7.21 (m, 1H) 6.62 (s, 2H); 13 C NMR ( MHz, CDCl 3 ): δ , , , , , , (C 2), (C 2), (C 2), (C 2), , , (C 2), (C 2) ; GC-MS m/e ,2-Dimethoxy-4-styryl-benzene: [17] Ph MeO OMe 1 H NMR ( MHz, CDCl 3, TMS): δ 7.49 (d, J = 7.56 Hz, 2H), 7.34 (t, J = 7.56 Hz, 2H), 7.23 (t, J = 7.56 Hz, 1H), (m, 3H), 6.97 (d, J = Hz, 1H), 6.84 (d, J = 8.28 Hz, 1H), 3.93 (s, 3H), 3.88 (s, 3H); 13 C NMR ( MHz, CDCl 3 ): δ , , , , (C 2), , , , (C 2), , , , 55.84, 55.71; GC-MS m/e Styryl-naphthalene: [18] Ph 1 H NMR ( MHz, CDCl 3, TMS): δ (m, 4H)), 7.74 (d, J = 8.22 Hz, 1H), 7.56 (d, J = 8.22 Hz, 2H), (m, 2H), 7.37 (t, J = 6.18 Hz, 2H), (m, 3H); 13 C NMR ( MHz, CDCl 3 ): δ , , , , , , (C 2), , , (C 2), , (C 2), , , ; GC-MS m/e Styryl-naphthalene: [1] Ph 1 H NMR ( MHz, CDCl 3, TMS): δ 8.20 (d, J = 8.22 Hz, 1H), (m, 2H), 7.78 (d, J = 8.22 Hz, 1H), 7.72 (d, J = 7.56 Hz, 1H), 7.58 (d, J = 7.56 Hz, 2H), (m, 3H), 7.38 ( t, J = 7.56 Hz, 2H), 7.28 ( t, J = 7.56 Hz, 1H), 7.13 (d, J = Hz, 1H); 13 C NMR ( MHz, 10
12 CDCl 3 ): δ , , , , , (C 2), , , , (C 2), , , , , , ; GC-MS m/e Styryl-furan: [19] O Ph 1 H NMR ( MHz, CDCl 3, TMS): 7.46 (d, J = 7.56 Hz, 2H), 7.40 (d, J = 1.32 Hz, 1H), 7.33 (t, J = 7.56 Hz, 2H), 7.23 (t, J = 7.56 Hz, 1H), 7.03 (d, J = Hz, 1H), 6.89 (d, J = Hz, 1H), 6.41 (d, J = 4.8 Hz, 1H), 6.35 (d, J = 4.8 Hz, 1H); 13 C NMR ( MHz, CDCl 3 ): δ , , , (C 2), , , (C 2), , , ; GC-MS m/e Styryl-thiophene: [16] S Ph 1 H NMR ( MHz, CDCl 3, TMS): δ 7.43 (d, J = 7.56 Hz, 2H), 7.32 (t, J = 7.56 Hz, 2H), 7.22 (t, J = 7.56 Hz, 1H), 7.20 (d, J = Hz, 1H), 7.15 (d, J = 4.80 Hz, 1H), 7.04 (d, J = 3.48 Hz, 1H), 6.97 (t, J = 3.48 Hz, 1H), 6.91 (d, J = Hz, 1H); 13 C NMR ( MHz, CDCl 3 ): δ , , (C 2), , (C 2), (C 2), , , ; GC-MS m/e Styryl-pyridine: [20] Ph N 1 H NMR ( MHz, CDCl 3, TMS): δ 8.72 (s, 1H), 8.48 (d, J = 2.04 Hz, 1H), 7.83 (t like, 1H), 7.53 (d, J = 7.56 Hz, 2H), 7.38 (t, J = 7.56 Hz, 2H), (m, 2H), 7.16 (d, J = Hz, 1H), 7.07 (d, J = Hz, 1H); 13 C NMR ( MHz, CDCl 3 ) δ (C 2), , , , , (C 2), , (C 2), , ; GC-MS m/e Styryl-benzo[1,3]dioxole: [21] O Ph O 1 H NMR ( MHz, CDCl 3, TMS): δ 7.47 (d, J = 7.56 Hz, 2H), 7.33 (t, J = 7.56 Hz, 2H),
13 (t, J = 7.56 Hz, 1H), 7.06 (d, J = 1.38 Hz, 1H), 7.01 (d, J = Hz, 1H), (m, 2H ), 6.79 (d, J = 7.56 Hz, 1H), 5.95 (s, 2H); 13 C NMR ( MHz, CDCl 3 ): δ , , , , (C 2), , , , (C 2), , , , ; GC-MS m/e (1E,3E)-1,4-Diphenylbuta-1,3-diene: [1] Ph 1 H NMR ( MHz, CDCl 3, TMS): δ 7.43 (d, J = 7.56 Hz, 4H), 7.32 (t, J = 7.56 Hz, 4H), 7.22 (t, J = 7.56 Hz, 2H), 6.94 (dd, J = 11.70, 2.76 Hz, 2H), 6.66 (dd, J = 11.70, 2.76 Hz, 2H); 13 C NMR ( MHz, CDCl 3 ): δ (C 2), (C 2), (C 2), (C 4), (C 2), (C 4); GC-MS m/e (2-Cyclohexyl-vinyl)-benzene: [22] Ph 1 H NMR ( MHz, CDCl 3, TMS): δ (m, 3H), (m, 3H), 5.26 (t, J = 7.56 Hz, 1H), 3.34 (d, J = 6.84 Hz, 2H), 2.24 ( (d, J = 5.28 Hz, 2H), 2.11 (d, J = 5.28 Hz, 2H), (m, 1H), (m, 3H), (m, 1H); 13 C NMR ( MHz, CDCl 3 ): δ , , (C 2), (C 2), , , 37.17, 33.38, 28.73, 28.61, 27.85, 26.91; GC-MS m/e Non-1-enyl-benzene: [23] C 6 H 13 Ph 1 H NMR ( MHz, CDCl 3, TMS): δ (m, 3H), (m, 3H), 5.51 (m, 1H), 3.32 (d, J = 6.18 Hz, 2H), 2.01 (d, J = 6.18 Hz, 2H), (m, 8H), (t, J = 6.18 Hz, 3H); 13 C NMR ( MHz, CDCl 3 ): δ , , (C 2), (C 2), , , 39.17, 32.63, 31.84, 29.55, 28.97, 22.75, 14.20; GC-MS m/e Phenyl-pent-4-enylamine: GC-MS m/e H 2 N Ph 12
14 Ethyl-benzene: GC-MS m/e Ethyl-4-methoxy-benzene: GC-MS m/e MeO 4-Ethyl-biphenyl: GC-MS m/e Ph 4-Ethyl-1,2-dimethoxy-benzene: GC-MS m/e MeO OMe 2-Ethyl-naphthalene: GC-MS m/e Ethyl-pyridine: GC-MS m/e N Propyl-benzene: GC-MS m/e ,2-Diphenylethane: GC-MS m/e Ph 13
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