S. Podder, S. Roy / Tetrahedron 63 (2007) 9146–9152
9151
(200 MHz, CDCl3) d (ppm) (ortho isomer) 4.12 (s, 2H,
CH2), 7.03–7.59 (m, 9H, ArH); (para isomer) 3.93 (s, 2H,
CH2), 7.03–7.59 (m, 9H, ArH). 13C NMR (54.6 MHz,
CDCl3) d (ppm) (ortho+para) 41.3, 41.7, 119.9, 124.9,
126.0, 126.2, 126.3, 127.4, 127.8, 128.4, 128.5, 128.8,
129.0, 130.6, 131.1, 131.5, 132.8, 139.4, 140.1, 140.4.
NMR (54.6 MHz, CDCl3) d (ppm) 20.5, 36.3, 115.6,
126.3, 126.7, 128.2, 128.6, 130.1, 131.5, 140.0, 151.4.
4.5.13. (4-Chlorobenzyl)thiophene (25) [2-isomer 63877-
95-2].24 Colorless oil; 1H NMR (200 MHz, CDCl3)
d (ppm) (2-isomer) 4.14 (s, 2H, CH2), 6.80–6.82 (m, 1H,
CH thiophene ring), 6.86–7.02 (m, 2H, CH thiophene
ring), 7.12–7.36 (m, 4H, ArH); (3-isomer) 3.97 (s, 2H,
CH2), 6.80–6.82 (m, 1H, CH thiophene ring), 6.86–7.02
(m, 2H, CH thiophene ring), 7.12–7.36 (m, 4H, ArH). 13C
NMR (54.6 MHz, CDCl3) d (ppm) (2-+3-isomers) 35.3,
35.8, 121.4, 124.1, 125.3, 125.8, 126.8, 128.2, 128.5,
128.6, 129.9, 130.0, 131.9, 132.3, 138.8, 139.0, 140.8, 143.3.
4.5.6. (4-Methylbenzyl)dimethylbenzene (18) [3-isomer
28952-43-4 and 4-isomer 28952-42-3].19 Colorless oil; 1H
NMR (200 MHz, CDCl3) d (ppm) (3-isomer) 2.13 (s, CH3),
2.22 (s, CH3), 2.28 (s, CH3), 2.31 (s, CH3), 3.97 (s, 2H,
CH2), 6.94–7.08 (m, 7H, ArH); (4-isomer) 2.22 (s, CH3),
2.31 (s, CH3), 3.87 (s, 2H, CH2), 6.94–7.08 (m, 7H, ArH).
13C NMR (54.6 MHz, CDCl3) d (ppm) (3-+4-isomer) 15.4,
19.3, 19.8, 20.7, 21.0, 39.6, 41.1, 125.4, 126.3, 128.0,
128.2, 128.5, 128.7, 129.1, 129.7, 130.2, 134.1, 135.3,
135.4, 136.5, 136.9, 138.5, 138.9.
4.5.14. (4-Methylbenzyl)naphthalene (26) [a-isomer
1
20204-71-1 and b-isomer 20204-73-3].25 White solid; H
NMR (200 MHz, CDCl3) d (ppm) (a-isomer) 2.31 (s, 3H,
CH3), 4.42 (s, 2H, CH2), 7.09–8.03 (11H, ArH); (b-isomer)
2.32 (s, 3H, CH3), 4.11 (s, 2H, CH2), 7.09–8.03 (11H, ArH).
13C NMR (54.6 MHz, CDCl3) d (ppm) (a+b) 21.0, 38.7,
41.8, 124.3, 125.3, 125.6, 126.0, 127.1, 127.3, 127.6,
127.7, 128.1, 128.7, 129.0, 129.2, 132.2, 134.0, 135.5,
137.0, 137.6.
4.5.7. (Diphenylmethyl)toluene (19) [o-isomer 17016-20-
5 and p-isomer 603-37-2].20 Colorless oil; 1H NMR
(200 MHz, CDCl3) d (ppm) (ortho isomer) 2.22 (s, 3H,
CH3), 5.71 (s, 1H, CH), 6.99–7.32 (m, 14H, Ph); (para iso-
mer) 2.34 (s, 3H, CH3), 5.54 (s, 1H, CH), 6.99–7.32 (m, 14H,
Ph). 13C NMR (54.6 MHz, CDCl3) d (ppm) (ortho+para)
19.9, 21.0, 53.6, 56.5, 126.2, 126.4, 128.3, 129.0, 129.4,
129.5, 129.6, 135.8, 141.0, 144.2.
4.5.15. 2-Hex-2-enyl-toluene (27) [o-isomer 496783-63-2
and p-isomer 496783-65-4].8b Colorless oil; 1H NMR
(200 MHz, CDCl3) d (ppm) (ortho+para) 0.87/0.88 (two
triplets, CH3), 1.31–1.44 (m, CH2), 1.99 (q,
3J(H,H)¼6.7 Hz, CH2), 2.28/2.31 (two singlet, CH3),
3.27–3.31 (m, CH2), 5.47–5.52 (m, CH]CH), 6.90–7.12
(m, ArH). 13C NMR (54.6 MHz, CDCl3) d (ppm) (ortho+
para) 13.6, 19.3, 20.9, 22.6, 34.6, 36.6, 38.6, 125.9, 126.0,
128.0, 128.3, 128.9, 129.2, 130.0, 131.6, 131.7, 135.3,
136.2, 138.0, 139.1.
4.5.8. 3-(Diphenylmethyl)-2,5-dimethylfuran (20). Light
yellow oil; H NMR (200 MHz, CDCl3) d (ppm) 2.08 (s,
1
3H, CH3), 2.17 (s, 3H, CH3), 5.19 (s, 1H, CH), 5.64 (s,
1H, CH furan ring), 7.12–7.31 (m, 10H, ArH). 13C NMR
(54.6 MHz, CDCl3) d (ppm) 11.7, 13.6, 47.5, 107.7, 121.8,
126.2, 128.3, 128.8, 144.1, 145.8, 149.2. Anal. (C19H18O)
calcd, C: 86.98, H: 6.92; found, C: 86.71, H: 7.01.
4.5.9. Triphenylmethane (21) [519-73-3].21 White solid;
mp 92–95 ꢀC; 1H NMR (200 MHz, CDCl3) d (ppm) 5.57 (s,
1H, CH), 7.00–7.35 (m, 15H, ArH). 13C NMR (54.6 MHz,
CDCl3) d (ppm) 56.9, 126.3, 128.3, 129.5, 143.9.
4.5.16. 2-But-2-enyl-1,4-dimethylbenzene (28) [37849-09-
1
5].26 Colorless oil; H NMR (200 MHz, CDCl3) d (ppm)
3
1.68 (d, J(H,H)¼5.9 Hz, 3H, CH3), 2.26 (s, 3H, CH3),
3
2.31 (s, 3H, CH3), 3.27 (d, J(H,H)¼5.5 Hz, 2H, CH2),
5.47–5.54 (m, 2H, CH:CH), 6.96–7.06 (m, 3H, ArH). 13C
NMR (54.6 MHz, CDCl3) d (ppm) (E+Z) 12.8, 17.8, 18.8,
20.9, 29.7, 31.0, 36.5, 124.5, 126.0, 126.7, 128.6, 129.3,
129.7, 130.0, 133.0, 135.3, 138.9.
4.5.10. (E)-1,4-Dimethyl-2-(3-phenyl-2-propenyl)benz-
ene (22) [189562-31-0].16a Colorless oil; 1H NMR
(200 MHz, CDCl3) d (ppm) 2.31 (s, 3H, CH3), 2.32 (s, 3H,
3
CH3), 3.51 (d, J(H,H)¼4.8 Hz, 2H, CH2), 6.34–6.38 (m,
2H, CH:CH), 7.00–7.10 (m, 3H, ArH), 7.20–7.39 (m, 5H,
ArH). 13C NMR (54.6 MHz, CDCl3) d (ppm) (E+Z) 18.9,
20.9, 29.7, 36.9, 126.1, 127.0, 128.5, 128.7, 130.0, 130.1,
130.8, 133.2, 135.5, 137.6, 138.0.
4.5.17. 2-Benzyl-1,3,5-trimethylbenzene (29) [4453-79-
1
6].27 Colorless oil; H NMR (200 MHz, CDCl3) d (ppm)
2.20 (s, 6H, CH3), 2.29 (s, 3H, CH3), 4.01 (s, 2H, CH2),
6.89 (s, 2H, ArH), 6.99–7.03 (m, 2H, ArH), 7.14–7.23 (m,
3H, ArH). 13C NMR (54.6 MHz, CDCl3) d (ppm) 20.1,
20.9, 34.7, 125.7, 127.8, 128.3, 128.9, 133.8, 135.6, 137.0,
140.1.
4.5.11. Benzyltoluene (23) [o-isomer 713-36-0 and p-iso-
mer 620-83-7].22 Colorless oil; 1H NMR (200 MHz,
CDCl3) d (ppm) (ortho isomer) 2.26 (s, 3H, CH3), 4.00 (s,
2H, CH2), 7.10–7.29 (m, 9H, ArH); (para isomer) 2.33 (s,
3H, CH3), 3.96 (s, 2H, CH2), 7.10–7.29 (m, 9H, ArH). 13
C
Acknowledgements
NMR (54.6 MHz, CDCl3) d (ppm) (ortho+para) 19.6,
21.0, 38.8, 40.8, 41.1, 125.9, 126.1, 127.0, 128.4, 128.7,
129.2, 129.6, 129.8, 130.1, 130.4, 131.7, 135.7, 136.5,
137.4, 138.3, 138.8, 139.8.
We thank DST for the financial support. Research fellowship
to S.P. (CSIR–SRF) is acknowledged.
4.5.12. 2-Benzyl-4-methylphenol (24) [716-96-1].23 Light
yellow oil; H NMR (200 MHz, CDCl3) d (ppm) 2.26 (s,
Supplementary data
1
3H, CH3), 3.96 (s, 2H, CH2), 6.67–6.71 (m, 1H, ArH),
6.91–6.94 (m, 2H, ArH), 7.20–7.30 (m, 5H, ArH). 13C
Supplementary data associated with this article can be found