The sydnone ring as an ortho-director of lithiation. Dilithiation of 3-phenylsydnone and trapping by electrophiles

Tetrahedron Letters

Volumn 38, Issue 7, 1997, Pages 1165-1168

  Turnbull, Kenneth ^a   Krein, Douglas M ^a  

^a WRIGHT STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

SYDNONE DERIVATIVE;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 0031575647     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00015-4     Document Type: Article

References (24)

1. 1. Stewart, F.H.C. Chem. Rev. 1964, 64, 129.
2. 2. Ohta, M. and Kato, H. in Nonbenzenoid Aromatics, Snyder, J.P., ed., Academic Press, Inc.: New York, NY, 1969, 1, 146
3. 3. Huisgen, R.; Grashey, R. Angew. Chem. 1962, 74, 29.
4. 4. Earl, J.C.; Mackney, A.W. J. Chem. Soc. 1935, 899.
5. 5. Gelvin, C.R.; Turnbull, K. Helv. Chim. Acta 1992, 75, 1931.
6. 6. Fuchigami, T.; Chen, C.S.; Nonaka, T.; Yeh, N.Y.; Tien, H.J. Bull. Chem. Soc. Jpn. 1986, 59, 483.
7. 7. Greco, C.V.; Pesce, M.; Franco, J.M. J. Heterocycl. Chem. 1966, 3, 391.
8. 8. Greco, C.V.; O'Reilly, B.P. J. Heterocycl. Chem. 1970, 7, 1433.
9. 9. Preston, P.N.; Turnbull, K. J. Chem. Soc., Perkin Trans, 1 1977, 1229; Burson, W.C., III; Jones, D.R.; Turnbull, K.; Preston, P.N. Synthesis 1991, 745; Lowe, J.D.; Turnbull, K. J. Heterocycl. Chem. 1986, 23, 125; Saljoughian, M.; Turnbull, K. J. Heterocycl. Chem. 1988, 25, 1817.
10. 9. Preston, P.N.; Turnbull, K. J. Chem. Soc., Perkin Trans, 1 1977, 1229; Burson, W.C., III; Jones, D.R.; Turnbull, K.; Preston, P.N. Synthesis 1991, 745; Lowe, J.D.; Turnbull, K. J. Heterocycl. Chem. 1986, 23, 125; Saljoughian, M.; Turnbull, K. J. Heterocycl. Chem. 1988, 25, 1817.
11. 9. Preston, P.N.; Turnbull, K. J. Chem. Soc., Perkin Trans, 1 1977, 1229; Burson, W.C., III; Jones, D.R.; Turnbull, K.; Preston, P.N. Synthesis 1991, 745; Lowe, J.D.; Turnbull, K. J. Heterocycl. Chem. 1986, 23, 125; Saljoughian, M.; Turnbull, K. J. Heterocycl. Chem. 1988, 25, 1817.
12. 9. Preston, P.N.; Turnbull, K. J. Chem. Soc., Perkin Trans, 1 1977, 1229; Burson, W.C., III; Jones, D.R.; Turnbull, K.; Preston, P.N. Synthesis 1991, 745; Lowe, J.D.; Turnbull, K. J. Heterocycl. Chem. 1986, 23, 125; Saljoughian, M.; Turnbull, K. J. Heterocycl. Chem. 1988, 25, 1817.
13. 10. Ugarkar, B.G.; Badami, B.V.; Puranik, G.S.; Bhat, K.G.S. Arch. Pharm. (Weinheim) 1978, 311, 109.
14. 11. Snieckus, V. Chem. Rev. 1990, 90, 879.
15. 17
16. 17
17. 13. Beak, P.; Snieckus, V. Acc. Chem. Res. 1982, 15, 306; Narasimhan, N.S.; Mali, R.S. Synthesis 1983, 957; Beak, P.; Meyers, A.I. Acc. Chem. Res. 1986, 19, 356; Narasimhan, N.S. and Mali, R.S. Top. Curr. Chem. 1987, 133, 63.
18. 13. Beak, P.; Snieckus, V. Acc. Chem. Res. 1982, 15, 306; Narasimhan, N.S.; Mali, R.S. Synthesis 1983, 957; Beak, P.; Meyers, A.I. Acc. Chem. Res. 1986, 19, 356; Narasimhan, N.S. and Mali, R.S. Top. Curr. Chem. 1987, 133, 63.
19. 13. Beak, P.; Snieckus, V. Acc. Chem. Res. 1982, 15, 306; Narasimhan, N.S.; Mali, R.S. Synthesis 1983, 957; Beak, P.; Meyers, A.I. Acc. Chem. Res. 1986, 19, 356; Narasimhan, N.S. and Mali, R.S. Top. Curr. Chem. 1987, 133, 63.
20. 13. Beak, P.; Snieckus, V. Acc. Chem. Res. 1982, 15, 306; Narasimhan, N.S.; Mali, R.S. Synthesis 1983, 957; Beak, P.; Meyers, A.I. Acc. Chem. Res. 1986, 19, 356; Narasimhan, N.S. and Mali, R.S. Top. Curr. Chem. 1987, 133, 63.
21. 14. Cheeseman, G.W.H.; Greenberg, S.G. J. Organomet. Chem. 1979, 166, 139.
22. 15. Turnbull, K.; Krein, D.M. Synthesis 1996, 1183.
23. 16. Tien, H.-J.; Fang, G.-M.; Lin, S.-T.; Tien, L.-L. J. Chin. Chem. Soc. 1992, 39, 107.
24. 17. We are grateful to a referee for bringing this reference to our attention.