PHOSPHORUS, SULFUR, AND SILICON
5
2.4 Hz, CH), 7.28–7.55 (8H, m, arom); 13C NMR (75.4 MHz, 7.33–7.51 (8H, m, arom); 13C NMR (75.4 MHz, CDCl3): δ
CDCl3): δ 33.53 (CH2), 126.43, 128.45, 128.54, 128.61, 130.48, 33.53 (CH2), 126.32, 126.38, 126.71, 128.52, 128.92, 129.29,
130.54, 131.76, 131.97, 132.01, 134.05 (aromatic carbons and 131.30, 131.61, 132.88, 133.12, 133.83, 133.93 (aromatic
4
=
=
=
=
C C), 168.28, 172.70 (2C O). (Z) Isomer: δ 3.10 (2H, d, JHH carbons and C C), 168.10, 171.95 (2C O). (Z) Isomer:
= 1.8 Hz, CH2), 7.59 (1H, t, 4JHH = 1.8 Hz, CH), 7.28–7.55 (8H, δ 3.71 (2H, d, JHH = 2.0 Hz, CH2), 7.53 (1H, t, JHH
=
4
4
m, arom).
2.0 Hz, CH), 7.33–7.51 (8H, m, arom).
(E) and (Z)-2-(m-chlorophenyl methylidene)-N-phenyl suc-
cinimide (4h): White Powder, (0.267 g, mp 234–236 °C, yield
References
90%); IR (KBr) (υmax, cm−1): 3047 ( CHstr.), 1699 (C O), 1600
=
=
=
(C C); Anal. calc. for C17H12ClNO2 (297.06): C 68.58, H 4.06,
1. Selva, M.; Perosa, A.; Noè, M. Organophosphorus Chemistry, Vol. 43;
Royal Society of Chemistry: UK, 2014, pp. 85-116.
2. Odinets, I. L. Organophosphorus Chemistry, Vol. 41; Royal Society of
Chemistry: UK, 2011, pp. 85-116.
3. Kolodiazhnyi, O. I. Phosphorus Ylides, Wiley-VCH: Weinheim, 1999,
pp. 478-494.
4. Schobert, R.; Siegfried, S.; Nieuwenhuyzen, M.; Milius, W.; Hampel, F.
J. Chem. Soc. Perkin Trans. 2000, 1, 1723-1733.
5. Wasserman, H. H.; Baldino, C. M.; Coats, S. J. J. Org. Chem. 1995, 60,
8231-8235.
6. Balema, V. P.; Wiench, J. W.; Pruski, M.; Pecharsky, V. K. J. Am. Chem.
Soc. 2002, 124, 6244-6245.
7. Johnson, A. W. Ylides and Imines of Phosphorus., Wiley: New York,
1993.
8. Hudson, R. F.; Chopard, P. A. Helv. Chim. Acta. 1963, 46, 2178-2185.
9. Hedaya, E.; Theodoropulos S. Tetrahedron Lett. 1968, 24, 2241-2254.
10. Cunha, S.; Kascheres, A. J. Braz. Chem. Soc. 2000, 11, 525-529.
11. Thompson, L.; Ellman, J. A. Chem. Rev. 1996, 96, 555-600.
12. Gordon, E. M.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gallop, M.
A. J. Med. Chem. 1994, 37, 1385-1401.
13. Ullah, E.; Nulty, J. M.; Sliwinski, M.; Robertson, A. Tetrahedron Lett.
2012, 53, 3990-3993.
14. Liu, H. L.; Jiang, H. F.; Xu, L.; Zhan, H. Y. Tetrahedron Lett. 2007, 48,
8371-8375.
15. Shuttleworth, S. J.; Allin, S. M.; Sharma, P. K. Synthesis 1997, 1217-
1239.
16. Burgess, K. Solid-Phase Organic Synthesis, Wiley-Interscience: New
York, 2000.
17. Adair, G. R. A.; Edwards, M. G.; Williams, J. M. J. Tetrahedron Lett.
2003, 44, 5523-5525.
18. Stawinska, M. K.; Sas, W. J. Chem. Res. (S) 1999, 694-695.
19. Mangaleswaran, S.; Argade, N. P. J. Chem. Soc., Perkin Trans.1 2001,
1764-1766.
20. Zheng, X. Q.; Han, B. F.; Wang, X. F.; Qiang, S.; Yang, C. L. Heterocyclic
Commun. 2011, 17, 73-78.
21. Liu, Y.; Zhang, W. Angew. Chem. Int. Ed., 2013, 52, 8, 2203-2206.
22. Deshmukh, G. B.; Patil, N. S.; Gaikwad, V. B.; Bhole, A. D.; Patil, S. V.
J. Chem. Pharm. Res. 2014, 6, 8, 393-399.
N 4.70; found: C 68.5, H 4.2, N 4.6; 1H NMR (300 MHz, CDCl3):
(E) Isomer: δ 3.68 (2H, d, 4JHH = 2.0 Hz, CH2), 7.54 (1H, t, 4JHH
= 2.0 Hz, CH), 7.31–7.48 (9H, m, arom); 13C NMR (75.4 MHz,
CDCl3): δ 34.16 (CH2), 124.56, 126.42, 128.29, 128.74, 129.22,
129.89, 130.30, 130.44, 131.82, 133.83, 135.22, 135.77 (aro-
=
=
matic carbons and C C), 169.69, 172.70 (2C O). (Z) Iso-
mer: δ 3.76 (2H, d, JHH = 2.4 Hz, CH2), 7.70 (1H, t, JHH
4
4
=
2.4 Hz, CH), 7.31–7.48 (9H, m, arom).
(E) and (Z)-2-(2-chloro-6-fluorophenyl methylidene)-N-
phenyl succinimide (4i): Red powder: (0.302 g, yield 96%); IR
(KBr) (υmax, cm−1): 3064 ( CHstr.), 1715 (C O), 1641 (C C);
Anal. calc. for C17H12ClFNO2 (315.05): C 64.67, H 3.51, N
4.44; found: C 64.9, H 3.8, N 4.3; 1H NMR (300 MHz, CDCl3):
=
=
=
4
(E) Isomer: δ 3.51 (2H, d, JHH = 2.4 Hz, CH2), 7.80 (1H, t,
4JHH = 2.4 Hz, CH), 7.10–7.58 (8H, m, arom); 13C NMR
(75.4 MHz, CDCl3): δ 33.95 (CH2), 118.07 (d, 2JC-F = 23.3 Hz,
4
3
Cortho), 125.86 (d, JC-F = 3.0 Hz, Cpara), 133.36 (d, JC-F
=
9.8 Hz, Cmeta), 126.42, 126.80, 128.67, 129.16, 130.04, 131.89
1
=
(aromatic carbons and C C), 161.53 (d, JC-F = 245 Hz, Cipso),
4
=
168.67, 172.74 (2C O). (Z) Isomer: δ 3.30 (2H, d, JHH = 2.0 Hz,
CH2), 7.30 (1H, t, 4JHH = 2.0 Hz, CH), 7.10–7.58 (8H, m, arom).
(E) and (Z)-2-(m-fluorophenyl methylidene)-N-phenyl suc-
cinimide (4j): Pale brown powder: (0.266 g, mp 176–178 °C,
yield 95%); IR (KBr) (υmax, cm−1): 3056 ( CHstr.), 1707 (C O),
=
=
=
1644 (C C); Anal. calc. for C17H12FNO2 (281.09): C 72.59, H
4.30, N 4.98; found: C 72.8, H 4.6, N 4.8; 1H NMR (300 MHz,
4
CDCl3): (E) Isomer: δ 3.76 (2H, d, JHH = 2.4 Hz, CH2), 7.70
(1H, t, 4JHH = 2.4 Hz, CH), 7.28–7.51 (9H, m, arom); 13C NMR
(75.4 MHz, CDCl3): δ 34.15 (CH2), 117.04 (d, 2JC-F = 22.6 Hz,
4
3
Cortho), 126.13 (d, JC-F = 3.0 Hz, Cpara), 133.43 (d, JC-F
=
8.2 Hz, Cmeta), 126.42, 128.73, 129.22, 130.14, 131.83, 134.07
23. Oda, M.; Nakamura, T.; Neha, M.; Miyawaki, D.; Ohta, A.; Kuroda, S.;
Miyatake, R. Eur. J. Org. Chem. 2014, 5976-5985.
24. Ha, M. Y.; Kim, J. A.; Park, Y. J.; Park, D.; Choi, Y. J.; Kim, J. M.; Chung,
K. W.; Han, Y. K.; Park, J. Y.; Lee, J. Y.; Moon, H. R.; Chung, H. Y. Med.
Chem. Commun. 2011, 2, 542-549.
25. Thiemann, T.; Watanabe, M.; Tanakaa, Y.; Mataka, S. New J. Chem.
2006, 30, 359-369.
26. Thiemann, T.; Watanabe, M.; Tanakaa, Y.; Mataka, S. New J. Chem.
2004, 28, 578-584.
27. Awad, B. M.; Abdallah, S. M.; Hefny, H. A.; Abdou, M. H.; Abd-
Elmonem, F. I.; Abd-Elmonem, N. A. Life Sci. J. 2012, 9, 4, 567-
570.
1
=
(aromatic carbons and C C), 164.59 (d, JC-F = 245.0 Hz, Cipso),
4
=
169.74, 172.70 (2C O). (Z) Isomer: δ 3.69 (2H, d, JHH = 2.0 Hz,
CH2), 7.53 (1H, t, 4JHH = 2.0 Hz, CH), 7.28–7.51 (9H, m, arom).
(E) and (Z)-2-(4-chloro-3-nitrophenyl methylidene)-
N-phenyl succinimide (4k): Brown powder: (0.322 g, mp
202–204 °C, yield 94%); IR (KBr) (υmax, cm−1): 3064 ( CHstr.),
=
=
=
1715 (C O), 1642 (C C); Anal. calc. for C17H12ClNO2
(342.04): C 59.57, H 3.23, N 8.17; found: C 59.9, H 3.6, N
8.1; H NMR (300 MHz, CDCl3): (E) Isomer: δ 3.77 (2H,
d, JHH = 2.4 Hz, CH2), 7.53 (1H, t, JHH = 2.4 Hz, CH),
1
4
4