The first example of 2,2-dilithiocyanocyclopropanes: generation from 2-bromo-2-sulfinylcyanocyclopropanes with tert-butyllithium, property, and a synthesis of fully substituted cyanocyclopropanes

Tetrahedron Letters

Volumn 48, Issue 10, 2007, Pages 1855-1858

  Fukushima, Iori ^a   Gouda, Youhei ^a   Satoh, Tsuyoshi ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

1,1 Dilithiocyclopropane; Bromine lithium exchange; Cyanocyclopropane; Geminal dianion; Sulfoxide lithium exchange

Indexed keywords

BROMINE; CYCLOPROPANE DERIVATIVE; LITHIUM; LITHIUM DERIVATIVE; SULFOXIDE; THIOCYANIC ACID DERIVATIVE; TOLUENE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; SYNTHESIS;

EID: 33846840821     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.12.148     Document Type: Article

References (25)

1. Some monographs concerning the chemistry of carbanions:. Stowell J.C. Carbanions in Organic Synthesis (1979), John Wiley and Sons, New York
2. In: Buncel E., and Durst T. (Eds). Comprehensive Carbanion Chemistry; Part A and B (1980-1984), Elsevier, Amsterdam
3. Wakefield B.J. Organolithium Methods (1988), Academic Press, London
4. Clayden J. Organolithiums: Selectivity for Synthesis (2002), Pergamon, Amsterdam
5. Wakefield B.J. Organomagnesium Methods in Organic Synthesis (1995), Academic Press, London
6. In: Richey Jr. H.G. (Ed). Grignard Reagents New Developments (2000), John Wiley and Sons, Chichester
7. Some selected recent reviews concerning the chemistry of carbanions:. Krief A. Tetrahedron 36 (1980) 2531
8. Katritzky A.R., and Qi M. Tetrahedron 54 (1998) 2647
9. Friesen R.W. J. Chem. Soc., Perkin Trans. 1 (2001) 1969
10. Najera C., Sansano J.M., and Yus M. Tetrahedron 59 (2003) 9255
11. Whisler M.C., MacNeil S., Snieckus V., and Beak P. Angew. Chem., Int. Ed. 43 (2004) 2206
12. Chinchilla R., Najera C., and Yus M. Tetrahedron 61 (2005) 3139
13. Thompson C.M., and Green D.L.C. Tetrahedron 47 (1991) 4223
14. Marek I., and Normant J.-F. Chem. Rev. 96 (1996) 3241
15. Collins J.B., Dill J.D., Jemmis E.D., Apeloig Y., Schleyer P.v.R., Seeger R., and Pople J.A. J. Am. Chem. Soc. 98 (1976) 5419
16. Frenking G. Chem. Phys. Lett. 111 (1984) 529
17. Watts J.D., and Stamper J.G. Tetrahedron 43 (1987) 1019
18. Kawa H., Manley B.C., and Lagow R.J. J. Am. Chem. Soc. 107 (1985) 5313
19. Satoh T., and Gouda Y. Tetrahedron Lett. 47 (2006) 2835
20. Satoh T., Takano K., Ota H., Someya H., Matsuda K., and Koyama M. Tetrahedron 54 (1998) 5557
21. Satoh T., Kawashima T., Takahashi S., and Sakai K. Tetrahedron 59 (2003) 9599
22. Hassner A., and Stumer C. Organic Synthesis Based on Name Reaction (2002), Pergamon, Amsterdam
23. Li J.J. Name Reactions (2002), Springer, Berlin
24. Satoh T. J. Synth. Org. Chem. Jpn. 54 (1996) 481
25. Hitchcock P.B., Rowlands G.J., and Parmar R. Chem. Commun. (2005) 4219