Lithium hydroxide as base in the Wittig reaction. A simple method for olefin synthesis

Tetrahedron

Volumn 64, Issue 20, 2008, Pages 4644-4648

  Antonioletti, R ^a   Bonadies, F ^b   Ciammaichella, A ^b   Viglianti, A ^a  

^a CNR   (Italy)

^b SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

1 (4 TOLYL) 1 PROPENE; 1 (4 TOLYL) 3 METHYL 1 BUTENE; 1 PHENYL 1,3 PENTADIENE; 1,3 DIPHENYL PROPENE; 1,4 DIPHENYL 1,3 BUTADIENE; 2 CYCLOHEXYL VINYL BENZENE; 2 STYRYL PYRIDINE; 3 METHYL 1 PHENYL 1 BUTENE; 3 STYRYL FURAN; 3 STYRYL THIOPHENE; 3,3 DIMETHL 1 PHENYL 1 BUTENE; 3,5 DIMETHOXYSTILBENE; 4 (4 TOLYL) 3 BUTEN 2 ONE; 4 (N,N DIMETHYLAMINO)STILBENE; 4 BROMO STILBENE; 4 HYDROXYSTILBENE; 4 METHOXY 4' METHYL STILBENE; 4 METHOXYSTILBENE; 4 METHYL 1 PHENYL 1,3 PENTADIENE; 4 METHYL 4' NITRO STILBENE; 4 METHYL CINNAMONITRILE; 4 METHYL STILBENE; 4 NITRO STILBENE; BROMINE DERIVATIVE; LITHIUM DERIVATIVE; LITHIUM HYDROXIDE; NON 1 ENYL BENZENE; PHOSPHONIUM DERIVATIVE; STILBENE DERIVATIVE; STYRENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; OLEFINATION; PRIORITY JOURNAL; SYNTHESIS; WITTIG REACTION;

EID: 41549124408     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.02.091     Document Type: Article

References (54)

1. Antonioletti R., Bonadies F., Orelli L.R., and Scettri A. Gazz. Chim. Ital. 122 (1992) 237
2. Bonadies F., Forcellese M.L., Locati L., Scettri A., and Scolamiero C. Gazz. Chim. Ital. 124 (1994) 467
3. Bonadies F., Cardilli A., Lattanzi A., Orelli L.R., and Scettri A. Tetrahedron Lett. 35 (1994) 3383
4. Bonadies F., Cardilli A., Lattanzi A., Pesci S., and Scettri A. Tetrahedron Lett. 36 (1995) 2839
5. Bonadies F., Scettri A., and Di Campli C. Tetrahedron Lett. 37 (1996) 1899
6. Lattanzi A., Orelli L.R., Barone P., Massa A., Iannece P., and Scettri A. Tetrahedron Lett. 44 (2003) 1333
7. Takacs J.M., Jaber M.R., Clement F., and Walters C.J. J. Org. Chem. 63 (1998) 6757
8. Smith M.B., and March J. March's Advanced Organic Chemistry. 5th ed. (2001), Wiley Interscience, New York, NY p 330
9. Sokolov M.P., Gazirov I.G., and Mavrin G.V. J. Gen. Chem. USSR (Engl. Transl.) 59 (1989) 921
10. Petrov E.S. Bull. Acad. Sci. USSR, Phys. Ser. (Engl. Transl.) 25 (1976) 517
11. Bestmann H.J. Chem. Ber. 95 (1962) 58
12. Issleib K., and Liuder R. Justus Liebigs Ann. Chem. 112 (1967) 707
13. Mastrynkova T.A., Alajeva H.A., Suerbayev H.A., Mastrosov V.I., and Petrovsky P.V. Phosphorus 1 (1971) 159
14. Larsen R.O., and Aksnes G. Phosphorus, Sulfur and Silicon (1983) 219
15. Alunni S. J. Chem. Res., Synop. (1986) 231
16. Cristan H.J., and Plenat F. In: Patai S., and Hartley F.R. (Eds). The Chemistry of Organophosphorus Compounds Vol. 3 (1994), Wiley Interscience, New York, NY 108
17. Ling-Chung S., Sales K.D., and Uteng J.H.P. J. Chem. Soc., Chem. Commun. (1990) 662
18. Kolodiazhnyi O.I. Phosphorus Ylides (1999), Wiley Interscience, New York, NY
19. Patai S., and Hartley F.R. The Chemistry of Organophosphorus Compounds Vol. 3 (1994), Wiley Interscience, New York, NY
20. Cadogan J.I.G. Organophosphorus Reagents in Organic Synthesis (1979), Academic, London
21. 13C NMR, δ (ppm): 137.9, 135.7, 129.9, 128.5, 127.8, 125.6, 68.7, 57.6, 53.0. MS, m/z: 266 (100), 248 (10.3), 218 (16.9), 199 (17.3), 189 (33.7), 183 (16.9), 145 (44.6), 91 (52.4), 77 (23.3).
22. 13C NMR.
23. Barrero A.F., Herrador M.M., Moral J.F.Q.d., Arteaga P., Akssira M., Hanbali F.El., Arteaga J.F., Dieguez H.R., and Sanchez E.M. J. Org. Chem. 72 (2007) 2251
24. Mahesh M., Murphy J.A., and Wessel H.P. J. Org. Chem. 70 (2005) 4118
25. Li J.-H., Li J.-L., Wang D.-P., Pi S.-F., Xie Y.-X., Zhang M.-B., and Hu X.-C. J. Org. Chem. 72 (2007) 2053
26. Cella R., and Stefani H.A. Tetrahedron 62 (2006) 5656
27. Linde C., Koliai N., Norrby P.-O., and Akermark B. Chem.-Eur. J. 8 (2002) 2568
28. Sugihara T., Satoh T., Miura M., and Nomura M. Adv. Synth. Catal. 346 (2004) 1765
29. Tarzia G., Duranti A., Tontini A., Piersanti G., Mor M., Rivara S., Plazzi P.V., Park C., Kathuria S., and Piomelli D. J. Med. Chem. 46 (2003) 2352
30. Cui X., Li Z., Tao C.-Z., Xu Y., Li J., Liu L., and Guo Q.-X. Org. Lett. 8 (2006) 2467
31. Aun C.E., Clarkson T.J., and Happer D.A.R. J. Chem. Soc., Perkin Trans. 2 (1990) 635
32. Roberts J.C., and Pincock J.A. J. Org. Chem. 69 (2004) 4279
33. Zeni G., Alves D., Braga A.L., Stefani H.A., and Nogueira C.W. Tetrahedron Lett. 45 (2004) 4823
34. Ishino Y., Mihara M., Nishihama S., and Nishiguchi I. Bull. Chem. Soc. Jpn. 71 (1998) 2669
35. Chen C., Wang B., and Munoz B. Synlett (2003) 2404
36. Molander G.A., and Bernardi C.R. J. Org. Chem. 67 (2002) 8424
37. Periasamy M., Prasad A.S.B., and Suseela Y. Tetrahedron 51 (1995) 2743
38. Farhat S., Zouev I., and Marek I. Tetrahedron 60 (2004) 1329
39. Jang Y.-J., Shih Y.-K., Liu J.-Y., Kuo W.-Y., and Yao C.-F. Chem.-Eur. J. 9 (2003) 2123
40. Goering H.N., Seitz E.P., and Tseng C.C. J. Org. Chem. 46 (1981) 5304
41. Liu J.-T., Jang Y.-J., Shih Y.-K., Hu S.-R., Chu C.-M., and Yao C.-F. J. Org. Chem. 66 (2001) 6021
42. Delcamp J.H., and White M.C. J. Am. Chem. Soc. 128 (2006) 15076
43. Banert K., Hagedorn M., Liedtke C., Melzer A., and Schoeffler C. Eur. J. Org. Chem. 2 (2000) 257
44. Parrish J.P., Jung Y.C., Shin II S., and Jung K.W. J. Org. Chem. 67 (2002) 7127
45. Kirmse W., and Kopannia S. J. Org. Chem. 63 (1998) 1178
46. Chinkov N., Majumdar S., and Marek I. J. Am. Chem. Soc. 125 (2003) 13258
47. Hattori T., Suzuki Y., Ito Y., Hotta D., and Miyano S. Tetrahedron 58 (2002) 5215
48. Cella R., Orfao A.T.G., and Stefani H.A. Tetrahedron Lett. 47 (2006) 5075
49. Mino T., Shirae Y., Sasai Y., Sakamoto M., and Fujita T. J. Org. Chem. 71 (2006) 6834
50. Buszek K.R., and Braun N. Org. Lett. 9 (2007) 707
51. Velder J., Ritter S., Lex J., and Schmalz H.-G. Synthesis 2 (2006) 273
52. Younes S., Tchani G., Baziard-Mouysset G., Stigliani J.L., and Payard M. Eur. J. Med. Chem. Chim. Ther. 29 (1994) 87
53. Chin C.S., Kim M., Won G., Jung H., and Lee H. J. Chem. Soc., Dalton Trans. 11 (2003) 2325
54. Yu J., Gaunt M.J., and Spencer J.B. J. Org. Chem. 67 (2002) 4627