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- Κανδάκη Φωτόπουλος
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1 Supporting information Spectroscopic data of compounds 1a-f Benzyl bromide (1a) Yield: 81%. Colorless oil. b.p o C/15 mmhg (Lit o C/13 mmhg). 1 1 H NMR (CDCl 3 ): δ 4.45 (2H, s, PhCH 2 Br), (5H, m, CH). 13 C NMR (CDCl 3 ): δ 33.7 (PhCH 2 Br), (CH-4), (CH-3,5), (CH-2,6), (C-1). IR (Nujol): 2954 (vs), 2924 (vs), 2854 (vs), 1462 (s), 1377 (s) cm -1. o-bis(bromomethyl)benzene (1b) Yield: 75%. White solid. m.p.: C (Lit o C). 2 1 H NMR (CDCl 3 ): δ 4.68 (4H, s, PhCH 2 Br), (4H, m, CH). 13 C NMR (CDCl 3 ): δ 30.1 (PhCH 2 Br), (CH-4,5), (CH-3.6), (C-1,2). IR (KBr): 1437 (w), 1419 (w), 1227 (s), 1198 (s), 848 (w), 750 (w) cm -1. m-bis(bromomethyl)benzene (1c) Yield: 58%. White solid. m.p.: C (Lit o C). 3 1 H NMR (CDCl 3 ): δ 4.48 (4H, s, PhCH 2 Br), 7.33 (3H, m, PhCH), 7.43 (1H, m, PhCH). 13 C NMR (CDCl 3 ): δ 33.0 (PhCH 2 Br), (CH-4,6), (CH-5), (CH-2), (C-1,3). IR (KBr): 1486 (w), 1436 (vs), 1210 (vs), 1163 (s), 898 (w), 798 (s) cm -1. p-bis(bromomethyl)benzene (1d) Yield: 15%. White solid. m.p.: C (Lit o C). 2 1 H NMR (CDCl 3 ): δ 4.48 (4H, s, PhCH 2 Br), 7.37 (4H, s, CH). 13 C NMR (CDCl 3 ): δ 33.0 (PhCH 2 Br), (CH-2,3,5,6), (C-1,4). IR (KBr): 2346 (s), 1456 (w), 1433 (w), 1221 (s), 1211 (s), 1187 (s), 766 (s), 738 (s) cm -1. 1,3,5-tris(Bromomethyl)benzene (1e) Yield: 42%. White solid. m.p.: C (Lit ). 4 1 H NMR (CDCl 3 ): δ 4.45 (6H, s, PhCH 2 Br), (3H, s, CH). 13 C NMR (CDCl 3 ): δ 32.4 (PhCH 2 Br), (CH-2, 4, 6), (C-1,3,5). IR (KBr): 1256 (vs), 1152 (s), 1026 (s), 973 (s), 727 (s) cm Bromo-2,4,6-tris(bromomethyl)benzene (1f) Yield: 38%. White solid. m.p.: C (Lit ). 5 1 H NMR (CDCl 3 ): δ 4.41 (2H, s, Ph-4-CH 2 Br), 4.61 (4H, s, Ph-2,6-CH 2 Br), 7.44 (2H, s, CH). 13 C NMR (CDCl 3 ): δ 31.3 (Ph-2,6-CH 2 Br), 33.4 (Ph-4-CH 2 Br), (C-1), (CH-3,5), (C-2,6), (C-4). IR (KBr): 3441 (vs), 1212 (s), 703 (s) cm -1.
2 NMR spectra of compounds 2a-g Perfluoro-tert-butoxymethylbenzene (2a) H NMR spectrum of 2a C NMR spectrum of 2a
3 F NMR spectrum of 2a
4 o-bis(perfluoro-tert-butoxymethyl)benzene (2b) f H NMR spectrum of 2b f C NMR spectrum of 2b
5 f F NMR spectrum of 2b
6 m-bis(perfluoro-tert-butoxylmethyl)benzene (2c) 1 H NMR spectrum of 2c C NMR spectrum of 2c
7 F NMR spectrum of 2c
8 p-bis(perfluoro-tert-butoxylmethyl)benzene (2d) H NMR spectrum of 2d 13 C NMR spectrum of 2d
9 F NMR spectrum of 2d
10 1,3,5-tris(Perfluoro-tert-butoxylmethyl)benzene (2e) H NMR spectrum of 2e 13 C NMR spectrum of 2e
11 F NMR spectrum of 2e
12 1-Bromo-2,4,6-tris(perfluoro-tert-butoxylmethyl)benzene (2f) 1 H NMR spectrum of 2f 13 C NMR spectrum of 2f
13 f f F NMR spectrum of 2f
14 2,6-bis(Perfluoro-tert-butoxylmethyl)pyridine (2g) H NMR spectrum of 2g C NMR spectrum of 2g
15 F NMR spectrum of 2g 1 T. Yokoyama, G. R. Wiley, S. I. Miller, J. Org. Chem. 1969, 34, W. Wenner, J. Org. Chem. 1952, 17, R. E. Benson, R. V. Lindsay Jnr., B. C. Anderson, J. Org. Chem. 1959, 81, Y. Yamagiwa, Y. Koreishi, S. Kiyozumi, M. Kobayashi, T. Kamikawa, Bull. Chem. Soc. Jpn. 1996, 69, D. M. Tal, S. J. D. Karlish, Tetrahedron. 1995, 51, 3823.
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