4140
M. Adib et al. / Tetrahedron 67 (2011) 4137e4140
4.2.11. N-(4-Pyridyl)triphenyliminophosphorane (3k). White solid,
mp 155e157 ꢂC (154e155 ꢂC),30 yield: 0.687 g, 97%. 1H NMR
CHmeta), 128.2 (d, 1JPC¼101.5 Hz, Cipso), 124.8, 120.9, 120.4, and 118.7
(4CH).
(500.1 MHz, CDCl3):
d
8.09 (2H, d, J¼5.2 Hz, 2CH), 7.72 (6H, dd,
3JHH¼7.6 Hz and JPH¼11.9 Hz, 6CHortho), 7.61 (3H, td, JHH¼7.3 Hz
and 5JPH¼1.8 Hz, 3CHpara), 7.47 (6H, td, 3JHH¼7.5 Hz and 4JPH¼3.0 Hz,
6CHmeta), 6.57 (2H, d, J¼5.2 Hz, 2CH). 13C NMR (125.8 MHz, CDCl3):
3
3
Acknowledgements
This research was supported by the Research Council of the
University of Tehran as a research project (6102036/1/03).
2
2
d
158.8 (d, JPC¼2.4 Hz, CeN]P), 148.8 (CH), 132.4 (d, JPC¼9.7 Hz,
CHortho), 131.9 (d, 4JPC¼2.4 Hz, CHpara), 129.4 (d, 1JPC¼99.9 Hz, Cipso),
128.3 (d, 3JPC¼12.1 Hz, CHmeta), 117.8 (d, JPC¼19.2 Hz, CH).
3
References and notes
4.2.12. N-(3-Pyrimidyl)triphenyliminophosphorane (3l). White solid,
mp 119e121 ꢂC (118e120 ꢂC),31 yield: 0.689 g, 97%. 1H NMR
1. (a) Huisgen, R. In The Adventure Playground of Mechanisms and Novel Reactions:
Profiles, Pathways and Dreams; Seeman, J. I., Ed.; American Chemical Society:
Washington, DC, 1994; p 62; (b) Huisgen, R.; Blaschke, H.; Brunn, E. Tetrahedron
Lett. 1966, 7, 405e409; (c) Brunn, E.; Huisgen, R. Angew. Chem., Int. Ed. Engl.
1969, 8, 513e515.
(500.1 MHz, CDCl3):
d
8.16 (1H, d, J¼1.0 Hz, CH), 7.98 (1H, dd, J¼5.6,
3 3
1.2 Hz, CH), 7.79 (6H, dd, JHH¼7.8 Hz and JPH¼12.0 Hz, 6CHortho),
3
5
7.52 (3H, dt, JHH¼7.6 Hz and JPH¼1.7 Hz, 3CHpara), 7.44 (6H, td,
3JHH¼7.8 Hz and 4JPH¼2.7 Hz, 6CHmeta), 6.83 (1H, d, J¼5.6 Hz, CH). 13
C
2. Morrison, D. C. J. Org. Chem. 1958, 23, 1072e1074.
3. (a) Mitsunobu, O. Synthesis 1981, 1e28; (b) Hughes, D. L. Org. Prep. Proced. Int.
1996, 28, 127e164; (c) Watanabe, T.; Gridnev, I. D.; Imamoto, T. Chirality 2000,
12, 346e351; (d) Tsunoda, T.; Ito, S. J. Synth. Org. Chem. Jpn. 1997, 55, 631e641.
4. Kolasa, T.; Miller, M. J. J. Org. Chem. 1987, 52, 4978e4984.
2
NMR (125.8 MHz, CDCl3):
d
168.2 (d, JPC¼6.4 Hz, CeN]P), 156.8
(CH),153.4 (d, 4JP¼4.4 Hz, CH),132.9 (d, 2JPC¼9.9 Hz, CHortho),131.8 (d,
4JPC¼2.5 Hz, CHpara), 128.8 (d, JPC¼100.2 Hz, Cipso), 128.3 (d,
1
5. Liu, Y.; Xu, C.; Liu, L. Synthesis 2003, 1335e1338.
3JPC¼12.1 Hz, CHmeta), 114.4 (d, 3JPC¼24.5 Hz, CH).
6. Otte, R. D.; Sakata, T.; Guzei, I. A.; Lee, D. Org. Lett. 2005, 7, 495e498.
7. Girard, M.; Murphy, P.; Tsou, N. Tetrahedron Lett. 2005, 46, 2449e2452.
8. (a) Nair, V.; Biju, A. T.; Abhilash, K. G.; Menon, R. S.; Suresh, E. Org. Lett. 2005, 7,
2121e2123; (b) Nair, V.; Biju, A. T.; Mathew, S. C. Synthesis 2007, 697e704.
9. Nair, V.; Mathew, S. C.; Biju, A. T.; Suresh, E. Angew. Chem., Int. Ed. 2007, 46,
2070e2073.
10. Nair, V.; Biju, A. T.; Vinod, A. U.; Suresh, E. Org. Lett. 2005, 7, 5139e5142.
11. Nair, V.; Biju, A. T.; Mohanan, K.; Suresh, E. Org. Lett. 2006, 8, 2213e2216.
12. Johnson, A. W. Ylides and Imines of Phosphorus; Wiley: New York, NY, 1993.
13. Johnson, A. W. Ylide Chemistry; Academic: New York, NY, 1966.
14. Gololobov, Y. G.; Kasuchin, L. F. Tetrahedron 1992, 48, 1353e1406.
15. Gusar, N. I. Russ. Chem. Rev. 1991, 60, 146e161.
4.2.13. N-(2-Pyrazyl)triphenyliminophosphorane (3m). White solid,
mp 177e178 ꢂC (180.5e182 ꢂC),29 yield: 0.689 g, 97%. 1H NMR
(500.1 MHz, CDCl3):
d
8.10 (1H, d, J¼4.6 Hz, CH), 7.81 (6H, dd,
3JHH¼7.8 Hz and 3JPH¼11.9 Hz, 6CHortho), 7.70 (1H, d, J¼1.2 Hz, CH),
3
7.66 (1H, dd, J¼4.6, 1.2 Hz, CH), 7.53 (3H, dt, JHH¼7.6 Hz and
5JPH¼1.8 Hz, 3CHpara), 7.42 (6H, td, JHH¼7.6 Hz and JPH¼2.7 Hz,
3
4
6CHmeta). 13C NMR (125.8 MHz, CDCl3):
d
160.2 (d, JPC¼6.7 Hz,
2
3
CeN]P), 142.0 (d, JPC¼25.5 Hz, CH), 141.1 (CH), 133.3 (d,
2JPC¼9.6 Hz, CHortho), 132.2 (CH), 131.8 (d, 4JPC¼2.6 Hz, CHpara), 129.6
(d, 1JPC¼99.1 Hz, Cipso), 128.8 (d, 3JPC¼12.0 Hz, CHmeta).
16. Staudinger, H.; Meyer, J. Helv. Chim. Acta 1919, 2, 635e646.
17. Dehnicke, K.; Strable, J. Polyhedron 1989, 8, 707e726; Palacios, F.; Alonso, C.;
Rubiales, G.; Villegas, M. Tetrahedron 2005, 61, 2779e2794; Palacios, F.; Alonso,
C.; Rubiales, G.; Villegas, M. Tetrahedron Lett. 2004, 45, 4031e4034; Blanco, G.;
Quintela, J. M.; Peinador, C. Tetrahedron 2008, 64, 1333e1344; Blanco, G.;
Quintela, J. M.; Peinador, C. Tetrahedron 2007, 63, 2034e2041; Blanco, G.; Seguí,
N.; Quintela, J. M.; Peinador, C.; Chas, M.; Toba, R. Tetrahedron 2006, 62,
11124e11135; Liu, H.; Wang, H. Q.; Ding, M. W.; Liu, Z. J.; Xiao, W. J. J. Fluorine
4.2.14. N-(1,3-Thiazol-2-yl)triphenyliminophosphorane (3n). Pale or-
ange needles, mp 140 ꢂC (139e141 ꢂC),23b yield: 0.684 g, 95%. 1H
3
NMR (500.1 MHz, CDCl3):
d
7.86 (6H, dd, JHH¼7.7 Hz and
ꢀ
ꢀ
ꢀ
ꢀ
Chem. 2006, 127, 1584e1590; Andujar Sanchez, C. M.; Jose Iglesias, M.; Perez
3JPH¼12.3 Hz, 6CHortho), 7.58 (3H, t, JHH¼7.2 Hz, 3CHpara), 7.50 (6H,
3
ꢀ
ꢀ
Alvarez, I. J.; Lopez Ortiz, F. Tetrahedron Lett. 2003, 44, 8441e8444; Zhao, J. F.;
Xie, C.; Xu, S. Z.; Ding, M. W.; Xiao, W. J. Org. Biomol. Chem. 2006, 4, 130e134.
18. Abel, E. W.; Mucklejohn, S. A. Phosphorus, Sulfur, and Silicon 1981, 9, 235e266.
19. Alkock, H. R. PhosphoruseNitrogen Compounds; Academic: New York, NY, 1972.
20. Scriven, E. F. V.; Turnbull, K. Chem. Rev. 1988, 88, 298e368.
dt, 4JPH¼2.3 Hz and 3JHH¼7.5 Hz, 6CHmeta), 7.01 (1H, d, 3JHH¼3.8 Hz,
CH), 6.43 (1H, dd, JPH¼3.6 Hz and JHH¼3.8 Hz, CH). 13C NMR
5
3
(125.8 MHz, CDCl3):
d 173.9 (CeN]P), 138.3 (CH), 133.1 (d,
2JPC¼9.9 Hz, CHortho), 132.2 (d, JPC¼2.5 Hz, CHpara), 128.8 (d,
4
21. Neilson, R. H.; Wisian-Nielson, P. Chem. Rev. 1988, 88, 541e562.
22. Adib, M.; Mohamadi, A.; Sheikhi, E.; Ansari, S.; Bijanzadeh, H. R. Synlett 2010,
1606e1608; Adib, M.; Ansari, S.; Feizi, S.; Bijanzadeh, H. R. Synlett 2010,
921e923; Adib, M.; Ansari, S.; Fatemi, S.; Bijanzadeh, H. R.; Zhu, L. G. Tetrahe-
dron 2010, 66, 2723e2727; Adib, M.; Ansari, S.; Mohammadi, A.; Bijanzadeh, H.
R. Tetrahedron Lett. 2010, 51, 30e32; Adib, M.; Ansari, S.; Feizi, S.; Asgarian
Damavandi, J.; Mirzaei, P. Synlett 2009, 3263e3266; Adib, M.; Mahdavi, M.;
Ansari, S.; Malihi, F.; Zhu, L. G.; Bijanzadeh, H. R. Tetrahedron Lett. 2009, 50,
7246e7248; Adib, M.; Sheibani, E.; Zhu, L. G.; Bijanzadeh, H. R. Tetrahedron Lett.
2009, 50, 4420e4422; Adib, M.; Sheibani, E.; Bijanzadeh, H. R.; Zhu, L. G. Tet-
rahedron 2008, 64, 10681e10686; Adib, M.; Sayahi, M. H.; Ziyadi, H.; Zhu, L. G.;
Bijanzadeh, H. R. Synthesis 2008, 3289e3294; Adib, M.; Mohammadi, B.; Bi-
janzadeh, H. R. Synlett 2008, 3180e3182; Adib, M.; Mohammadi, B.; Bijanzadeh,
H. R. Synlett 2008, 177e180; Adib, M.; Sayahi, M. H.; Ziyadi, H.; Bijanzadeh, H.
R.; Zhu, L. G. Tetrahedron 2007, 63, 11135e11140.
23. (a) Yavari, I.; Adib, M.; Hojabri, L. Tetrahedron 2002, 58, 7213e7219; (b) Adib,
M.; Mostofi, M.; Ghanbary, K.; Bijanzadeh, H. R. Synthesis 2005, 1663e1667.
24. Mitsunobu, O.; Yamada, Y. Bull. Chem. Soc. Jpn. 1967, 40, 2380e2382.
25. Castro, B. R. Org. React. 1983, 29, 1e162.
26. Hughes, D. L. Org. React. 1992, 42, 335e656.
27. Kumara Swamy, K. C.; Bhuvan Kumar, N. N.; Balaraman, E.; Pavan Kumar, K. V. P.
Chem. Rev. 2009, 109, 2551e2651.
1JPC¼101.1 Hz, Cipso), 128.7 (d, 3JPC¼12.3 Hz, CHmeta), 108.8 (CH).
4.2.15. N-(4-Methyl-1,3-thiazol-2-yl)triphenyliminophosphorane
(3o). Pale orange needles, mp 159e160 ꢂC (157e159 ꢂC),23b yield:
0.696 g, 93%. 1H NMR (500.1 MHz, CDCl3):
d 7.86 (6H, dd,
3
3
3JHH¼7.6 Hz and JPH¼12.3 Hz, 6CHortho), 7.56 (3H, t, JHH¼6.8 Hz,
4
3
3CHpara), 7.47 (6H, dt, JPH¼2.6 Hz and JHH¼7.5 Hz, 6CHmeta), 5.95
(1H, s, CH), 2.16 (3H, s, CH3). 13C NMR (125.8 MHz, CDCl3):
d 171.6
2
(CeN]P), 148.0 (CH3eC), 133.2 (d, JPC¼10.1 Hz, CHortho), 132.2 (d,
4JPC¼2.6 Hz, CHpara), 128.6 (d, JPC¼101.4 Hz, Cipso), 128.6 (d,
1
3JPC¼12.3 Hz, CHmeta), 102.8 (CH), 17.7 (CH3).
4.2.16. N-(1,3-Benzothiazol-2-yl)triphenyliminophosphorane
(3p). Pale yellow solid, mp 148e149 ꢂC (138e144 ꢂC),23b yield:
0.780 g, 95%. 1H NMR (500.1 MHz, CDCl3):
d 7.94 (6H, dd,
3
3
3JHH¼8.1 Hz and JPH¼12.4 Hz, 6CHortho), 7.61 (3H, t, JHH¼7.4 Hz,
3CHpara), 7.55e7.50 (7H, m, CH and 6CHmeta), 7.48 (1H, d, J¼8.0 Hz,
CH), 7.23 (1H, t, J¼7.5 Hz, CH), 7.05 (1H, t, J¼7.5 Hz, CH). 13C NMR
28. Johnson, A. W.; Wong, S. C. K. Can. J. Chem. 1966, 44, 2793e2803.
29. Okawa, T.; Osakada, N.; Eguchi, S.; Kakehi, A. Tetrahedron 1997, 53,
16061e16082.
30. Balandier, J. Y.; Belyasmine, A.; Salle, M. Eur. J. Org. Chem. 2008, 269e276.
31. Lu, X.; Petersen, J. L.; Wang, K. K. J. Org. Chem. 2002, 67, 7797e7801.
(125.8 MHz, CDCl3):
d 171.4 (CeN]P), 152.8 and 134.0 (2C), 133.3
ꢀ
2
3
(d, JPC¼10.3 Hz, CHortho), 132.5 (CHpara), 128.7 (d, JPC¼12.5 Hz,