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R. Suau et al. / Tetrahedron 59 (2003) 2913–2919
1711; dH (CDCl3) 7.75–7.60 (m, 4H, ArH), 7.59–7.09 (m,
10H, ArH), 5.65 (dd, 1H, J¼11.1, 5.7 Hz, H10), 4.00 (dd,
1H, J¼13.9, 11.1 Hz, H20), 3.50 (dd, 1H, J¼13.9, 11.1 Hz,
H20); dC (CDCl3) 168.2 (C1, C3), 139.3, 137.9 (C100, C200),
131.7 (C3a, C7a), 133.8, 128.9, 128.7, 128.6, 128.5, 128.1,
127.9, 126.6, 123.1 (ArCH), 56.0 (NCH), 37.1 (CH2); m/z
(EI) 327 (Mþ, 11), 180 (100).
styrene (0.5 mL) was irradiated for 45 min. The reaction
mixture was worked up as above and the crude product
chromatographed, compound 4-d1 (32 mg) was isolated.
3.13.1. 2-(2-Deutero-2-phenylpropyl)-1H-isoindole-
1,3(2H)-dione (4-d1). dH (CDCl3) 7.8–7.6 (m, 4H, ArH),
7.25 (m, 5H, ArH), 3.90 (d, 1H, J¼13.4 Hz, NCH), 3.80 (d,
1H, J¼13.4 Hz, NCH), 1.35 (s, 3H, CH3); dC (CDCl3) 168.2
(C1, C3), 0143.3 (C30), 133.8 (C5, C6), 131.8 (C3a, C7a),
128.4 (C5 , C70), 127.2 (C40, C80), 123.1 (C4, C7), 126.7
(C60), 44.7 (CH2), 18.9 (CH3); m/z (EI) 266 (Mþ, 36), 160
(100), 119 (24).
3.9. With 4-methoxy-styrene
3.9.1. 2-[(4-Methoxyphenyl)ethyl]-1H-isoindole-1,3(2H)-
dione (8). White crystals; mp 135–1368C (MeOH) [lit.,23
139–1408C]; [Found: C 72.40, H 5.41, N 4.90. C17H15NO3
requires C 72.58, H 5.37, N 4.98]; nmax (neat) cm21 1767,
1703; dC (CDCl3) 168.0 (C1, C3), 158.2 (C60), 133.7, 129.7,
123.0, 113.8 (C4–C7, C40, C50, C70, C80), 131.9, 129.9
(C3a, C7a, C30), 55.0 (OCH3), 39.3 (CH), 33.5 (CH2); m/z
(EI) 281 (Mþ, 1), 134 (100).
Acknowledgements
The authors wish to acknowledge financial support from
Spain’s DGES (project PB97-1077). and DGI (project
BQU2001-1890).
3.10. With trans-anethole
3.10.1. 2-[(4-Methoxyphenyl)-1-methylethyl]-1H-iso-
indole-1,3(2H)-dione (9). White crystals; mp 61–628C
(CHCl3); [Found: C 72.77, H 5.88, N 4.82. C18H17NO3
requires C 73.20, H 5.80, N 4.74]; nmax (neat) cm21 1769,
1690; dH (CDCl3) 7.80–7.60 (m, 4H, ArH), 7.09 (d, 2H,
J¼8.6 Hz, H40, H80) 6.72 (d, 2H, J¼8.6 Hz, H50, H70), 4.59
(m, 1H, NCH), 3.72(s, 1H, OCH3), 3.26 (dd, 1H, J¼13.5,
9.4 Hz, H20), 3.02 (dd, 1H, J¼13.5, 6.8 Hz, H20), 1.51 (d,
3H, J¼6.8 Hz, CH3); dC (CDCl3) 168.3 (C1, C3), 158.1
(C60), 131.8, 130.4 0(C30,0 C3a, C7a), 133.7, 129.8, 122.9,
113.7 (C4–C7, C4 , C8 , C50, C70), 55.1 (OCH3), 48.7
(NCH), 38.9 (CH2), 18.2 (CH3); m/z (EI) 295 (Mþ, 6), 174
(100), 148 (84), 121 (48).
References
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3.11. With isosafrole
3.11.1. 2-(1,3-Benzodioxol-5-yl-1-methylethyl)-1H-iso-
indole-1,3(2H)-dione (10). Syrup; nmax (neat) cm21 1765,
1688; dH (CDCl3) 7.80–7.60 (m, 4H, ArH), 6.65 (m, 3H,
ArH), 5.85 (s, 2H, OCH2O), 4.57 (m, 1H, H10), 3.24 (dd, 1H,
J¼13.8, 9.3 Hz, H20), 2.98 (dd, 1H, J¼13.8, 6.7 Hz, H20),
1.50 (d, 3H, J¼7.0 Hz, CH3); dC (CDCl3) 168.4 (C1, C3),
147.6, 146.1 (C50, C60), 132.1, 131.9 (C30, C3a, C7a), 1330.7
(C5, C6), 123.0 (C4, C7), 121.9, 109.3, 108 (C40, C80, C7 ),
100.8 (OCH2O), 48.8 (NCH), 38.6 (CH2), 18.2 (CH3); m/z
(EI) 309 (Mþ, 12), 174 (100), 162 (5), 147 (15); EI-HRMS
calcd for C18H15NO4 309.1001, found 309.1008.
3. (a) Mazzocchi, P. H.; Minamikawa, S.; Wilson, P. J. Org.
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3.12. With indene
3.12.1. 2-(2,3-Dihydro-1H-inden-2-yl)-1H-isoindole-
1,3(2H)-dione (11). White needles; mp 196–1978C
(EtOH) [lit.,24 194–1958C (CH2Cl2/hexane)]; [Found: C
77.20, H 4.94, N 5.30. C17H13NO2 requires C 77.55, H 4.98,
N 5.32]; nmax (neat) cm21 1767, 1698; m/z (EI) 263 (Mþ,
20), 116 (100).
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3.13. Irradiation in CH3CN/D2O
´
(b) Suau, R.; Garcıa-Segura, R.; Sosa-Olaya, F. Tetrahedron
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The homogeneous solution consisting of phthalimide
(100 mg, 0.68 mmol), NaOH (0.05 mL of a 1 M solution),
13 mL of acetonitrile, 2 mL of 99% D2O and a-methyl-
´ ´ ´ ´
6. Suau, R.; Sanchez-Sanchez, C.; Garcıa-Segura, R.; Perez-
Inestrosa, E. Eur. J. Org. Chem. 2002, 1903–1911.