Nucleophilic substitution at an sp2 carbon of vinyl halides with an intramolecular thiolate moiety: synthesis of 2-alkylidenethietanes

Tetrahedron Letters

Volumn 49, Issue 26, 2008, Pages 4125-4129

  Lei, Mao Yi ^a   Fukamizu, Koji ^b   Xiao, Yong Jun ^a   Liu, Wei Min ^a   Twiddy, Scott ^a   Chiba, Shunsuke ^a   Ando, Kaori ^c   Narasaka, Koichi ^a  

^a Nanyang Technological University   (Singapore)

^b UNIVERSITY OF TOKYO   (Japan)

^c GIFU UNIVERSITY   (Japan)

Author keywords

2 Alkylidenethietane; Density functional theory (DFT); Nucleophilic vinylic substitution; SNV mechanism

Indexed keywords

CARBON; HALIDE; THIETANE DERIVATIVE;

ARTICLE; SUBSTITUTION REACTION; SYNTHESIS;

EID: 44149101635     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.04.127     Document Type: Article

References (33)

1. E.D. Hughes F. Juliusburger S. Masterman B. Topley J. Weiss J. Chem. Soc. 1935 1525
2. (a) For reviews, see: Z. Rapport Acc. Chem. Res. 25 1992 474
3. (b) T. Okuyama G. Lodder T.T. Tidwell J.P. Richard Advances in Physical Organic Chemistry Vol. 37 2002 Academic Press New York 1 56
4. (c) T. Okuyama J. Synth. Org. Chem. Jpn. 64 2006 348
5. (a) S.I. Miller P.K. Yonan J. Am. Chem. Soc. 79 1957 5931
6. (b) S.I. Miller V. Gold Advances in Physical Organic Chemistry Vol. 6 1968 Academic Press New York 185 332
7. (c) D.R. Kelsey R.G. Bergman J. Am. Chem. Soc. 93 1971 1953
8. (a) M.N. Glukhovtsev A. Pross L. Radom J. Am. Chem. Soc. 116 1994 5961
9. (b) V. Lucchini G. Modena L. Pasquato J. Am. Chem. Soc. 117 1995 2297
10. (c) C.K. Kim K.H. Hyun C.K. Kim I. Lee J. Am. Chem. Soc. 122 2000 2294
11. (d) R.D. Bach A.G. Baboul H.B. Schlegel J. Am. Chem. Soc. 123 2001 5787
12. (a) It was reported that intermolecular substitution reactions of β-halostyrenes with thiolate and selenide anions occur with retention of the configuration, but the reaction mechanisms were not revealed, see: G. Marchese F. Naso G. Modena J. Chem. Soc. B 1968 958
13. (b) G. Marchese F. Naso G. Modena J. Chem. Soc. B 1969 290
14. (c) M. Tiecco L. Testaferri M. Tingoli D. Chianelli M. Montanucci Tetrahedron Lett. 25 1984 4975
15. (a) M. Ochiai K. Oshima Y. Masaki J. Am. Chem. Soc. 113 1991 7059
16. (b) T. Okuyama T. Takino K. Sato M. Ochiai J. Am. Chem. Soc. 120 1998 2275
17. (c) M. Ochiai Y. Nishi M. Hirobe Tetrahedron Lett. 46 2005 1863
18. J.J. Shiers M. Shipman J.F. Hayes A.M.Z. Slawin J. Am. Chem. Soc. 126 2004 6868
19. (a) K. Ando M. Kitamura K. Miura K. Narasaka Org. Lett. 6 2004 2461
20. (b) H. Miyauchi S. Chiba K. Fukamizu K. Ando K. Narasaka Tetrahedron 63 2007 5940
21. (a) For reports on the synthesis of 2-alkylidenethietane derivatives, see: J. Bolster R.M. Kellogg J. Org. Chem. 45 1980 4804
22. (b) B.F. Bonini M.C. Franchini M. Fochi S. Mangini G. Mazzanti A. Alfredo Ricci Eur. J. Org. Chem. 2000 2391
23. (c) S. Ozaki E. Matsui T. Saiki H. Yoshinaga H. Ohmori Tetrahedron Lett. 39 1998 8121
24. T. Mandai J. Nokami T. Yano Y. Yoshinaga J. Otera J. Org. Chem. 49 1984 172
25. J. Uenishi M. Ohmi Heterocycles 61 2003 365
26. W.J. Moree G.A. van der Marel R.J. Liskamp J. Org. Chem. 60 1995 5157
27. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. gaussian 03, Revision C.02, Gaussian, Wallingford, CT, 2004.
28. (a) A.D. Becke J. Chem. Phys. 96 1992 2155
29. (b) C. Lee W. Yang R.G. Parr Phys. Rev. B 37 1988 785
30. (a) L. Onsager J. Am. Chem. Soc. 58 1936 1486
31. (b) M.W. Wong M.J. Frisch K.B. Wiberg J. Am. Chem. Soc. 113 1991 4776
32. C. Fu S. Ma Eur. J. Org. Chem. 2005 3942
33. S. Ma H. Xie G. Wang J. Zhang Z. Shi Synthesis 5 2001 713