Reaction of ammonium ylides with alkyl thiocyanates
411
15. Meffre P, Vo Quang Y, Le Goffic F (1990) Tetrahedron Lett
31:2291
16. Truce WE, Knospe R (1955) J Am Chem Soc 77:5063
17. Kharasch N, Wehrmeister HL, Tigerman H (1976) J Am Chem
Soc 98:17
18. Havlik AJ, Kharasch N (1956) J Am Chem Soc 78:1207
19. Chivers JCA, Smlles S (1928) J Chem Soc 697
20. Barltrop JA, Mogan KJ (1960) J Chem Soc 4486
21. Scholz D (1983) Synthesis 944
22. Seebach D, Teschner M (1973) Tetrahedron Lett 14:5113
23. Groenewegen P, Kallenberg H, van der Gen A (1979) Tetrahe-
dron Lett 20:2817
the mixture was stirred at r.t. for 7 h. To this mixture
0.40 g K2CO3 (2.90 mmol) was added, and after 30 min
0.10 g methyl thiocyanate (1.15 mmol) was added and
allowed to stir at reflux for 8 h. The reaction solution was
extracted with dichloromethane. The combined organic
layer was dried over sodium sulfate and concentrated under
reduced pressure. The crude oil was purified by passing
through a column of silica gel, eluting with 10 % EtOAc in
n-hexane to afford 2a as yellow oil (53 %); b.p.: 110 °C.
p-Methoxy-2-(methylthio)acetophenone (2d)
Yellow liquid (54%); b.p.: 175 °C.
24. Coates RM, Pigott HD, Ollinger J (1974) Tetrahedron Lett
15:3955
25. Huang C-H, Liao K-S, De SK, Tsai Y-M (2000) Tetrahedron Lett
41:3911
26. Anastas PT, Warner JC (1998) Green chemistry: theory and
practice. Oxford University Press, Oxford
27. Li CJ, Chan TH (1997) Organic reactions in aqueous media.
Wiley, New York
28. Li CJ, Chan TH (1999) Tetrahedron 55:11149
29. Li CJ (1993) Chem Rev 93:2023
p-Bromo-2-(ethylthio)acetophenone (2g)
Yellow crystals (55%); m.p.: 145–150 °C.
2-(Ethylthio)-p-phenylacetophenone (2i, C16H16OS)
Light yellow crystals (49%); m.p.: 67-69 °C; 1H NMR
(500.1 MHz, CDCl3): d = 1.33 (t, J = 7.4 Hz, 3H), 2.66
(q, J = 7.4 Hz, 2H), 3.87 (s, 2H), 7.45 (m, 1H), 7.52
(t, J = 7.3 Hz, 2H), 7.67 (d, J = 7.0 Hz, 2H), 7.74
(d, J = 8.3 Hz, 2H), 8.10 (d, J = 8.3 Hz, 2H) ppm; 13C
NMR (125.7 MHz, CDCl3): d = 14.6, 26.8, 37.2, 127.71,
127.74, 128.7, 129.4, 129.8, 134.4, 140.3, 146.5,
194.6 ppm; IR (KBr): v = 2,956, 1,672, 1,267, 1,122,
1,039, 740 cm-1; MS: m/z = 256 (M?, 5), 223 (23), 196
(79), 181 (100), 152 (97), 127 (13), 83 (19).
30. Yao X, Li C (2005) Org Lett 7:4395
31. Li CJ (2005) Chem Rev 105:3095
¨
32. Lindstrom UM (2002) Chem Rev 102:2751
33. Tomilov YV, Platonov DN, Dorokhov DV, Nefedov OM (2007)
Tetrahedron Lett 48:883
34. Vanecko JA, Wan H, West FG (2006) Tetrahedron 62:1043
35. Troshin PA, Peregudov AS, Peregudov SM, Lyubovskaya RN
(2007) Eur J Org Chem 35:5861
36. Li AH, Dai LX (1997) Chem Rev 97:2341
37. Curphey TJ, Libby AH (2000) Tetrahedron Lett 41:6977
38. Song HM, Kim K (2002) J Chem Soc Perkin Trans 1 2414
39. Yu H, Dong D, Ouyang Y, Wang Y, Liu Q (2007) Synlett 151
40. Arisawa M, Suwa K, Yamaguchi M (2009) Org Lett 11:625
41. Debenham SD, Chan A, Liu K, Price K, Wood HB (2005) Tet-
rahedron Lett 46:2283
Acknowledgments Financial support by the research council of the
University of Tehran is gratefully acknowledged. We thank Dr. Karol
Gajewski for helpful advice with this work.
42. Andrieux CP, Saveant J-M, Tallec A, Tardivel R, Tardy C (1997)
J Am Chem Soc 119:2420
43. Jouen C, Pommelet JC (1997) Tetrahedron 53:12565
44. Griesbaum K, Oswald AA, Hudson BE (1963) J Am Chem Soc
85:1969
References
1. Trost BM (1978) Chem Rev 78:363
45. Loghmani-Khouzani H, Poorheravi MR, Sadeghi MMM, Caggi-
ano L, Jackson RFW (2008) Tetrahedron 64:7419
46. Huang X, Zheng W-X (1999) Synthetic Commun 29:1297
47. Ranu BC, Mandal T, Banerjee S, Dey SS (2007) Aust J Chem
60:278
2. Trost BM (1978) Acc Chem Res 11:453
3. Kane VV, Singh V, Martin A, Doyle DL (1983) Tetrahedron
39:345
4. Trost BM, Salzmann TN, Hiroi K (1976) J Am Chem Soc
98:4887
48. Vedejs E, Eberlein TH, Mazur DJ, McClure CK, Perry DA,
Ruggeri R, Schwartz E, Stults JS, Varie DL (1986) J Org Chem
51:1556
49. Ishibashi H, Matsuoka K, Ikeda M (1989) Synthetic Commun
19:443
5. Woodward RB, Pachter IJ, Scheinbaum ML (1971) J Org Chem
36:1137
6. Carre MC, Caubere P (1985) Tetrahedron Lett 26:3103
7. Kano S, Yokomatsu T, Shibuya S (1978) Tetrahedron Lett
19:4125
50. Kunugi A, Takahashi N, Abe K, Hirai T (1989) Bull Chem Soc
Jpn 62:2055
51. Dehmel F, Ciossek T, Maier T, Weinbrenner S, Schmidt B,
Zoche M, Beckers T (2007) Bioorg Med Chem Lett 17:4746
52. Olivato PR, Wladislaw B, Guerrero SA (1987) Phosphorus,
Sulfur Relat Elem 33:135
53. Saikachi M (1969) Chem Pharm Bull 17:1260
54. Floyd MB, Du MT, Fabio PF, Jacob LA, Johnson BD (1985) J
Org Chem 50:5022
8. Sunder S, Peet NP, Trepanies DL (1967) J Org Chem 41:2712
9. Sheibley FE (1952) J Org Chem 17:221
10. Nagao Y, Ochiai M, Kaneko K, Maeda A, Watanabe K, Fujita E
(1977) Tetrahedron Lett 18:1345
11. Coates RM (1973) Angew Chem Int Ed 12:586
12. Krafft GA, Meinke PT (1985) Tetrahedron Lett 26:135
13. Luly JR, Yi N, Soderquist J, Stein H, Cohen J, Perun TJ, Plattner
JJ (1987) J Med Chem 30:1609
14. Conchillo A, Camps F, Messeguer A (1990) J Org Chem 55:1728
123