A Novel Intramolecular Cyclopropanation Using Iodonium Ylides

Journal of the American Chemical Society

Volumn 111, Issue 16, 1989, Pages 6443-6444

  Moriarty, Robert M ^a   Vaid, Radhe K ^a   Zhao, Lei ^a   Prakash, Om ^b  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

^b KURUKSHETRA UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001519750     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00198a078     Document Type: Article

References (23)

1. Stork, G.; Ficini, J. J. Am. Chem. Soc. 1961, 83, 4678.
2. Burke, S. D.; Grieco, P. A. Org. React. 1987, 26, 361.
3. Maas, G. Top. Curr. Chem. 1987, 137, 75.
4. Hudlicky, T.; Rami, B. C. J. Org. Chem. 1985, 50, 123 and references contained therein.
5. Taber, D. F.; Krewson, K. R.; Roman, K.; Rheingold, A. L. Tetrahedron Lett. 1984, 25, 5283.
6. Chen, E. Y. J. Org. Chem. 1984, 49, 3245.
7. Kang, S. H.; Kim, W. J.; Chae, Y. B. Tetrahedron Lett. 1988, 29, 5169.
8. Moriarty, R. M.; Bailey, B. R., III; Prakash, O.; Prakash, I. J. Am. Chem. Soc. 1985, 107, 1375.
9. Sax, N. I. Dangerous Properties of Industrial Materials, 5th ed.; Van Nostrand Reinhold: New York, 1979; pp 544–546. Bretherick, L. Handbook of Reactive Chemical Hazards, 2nd ed.; Butterworth: London, Boston, 1979; pp 589–590.
10. Hadjiarapoglou, L. Tetrahedron Lett. 1987, 4449. Papadopoulou, M.; Spyroudis, S.; Varvoglis, A. J. Org. Chem. 1985, 50, 1509.
11. Koser, G. F.; Yu, S.-M. J. Org. Chem. 1975, 40, 1166.
12. Spyroudis, S. P. J. Org. Chem. 1986, 51, 3453.
13. Stork, G.; Szajewski, R. P. J. Am. Chem. Soc. 1974, 96, 5787.
14. Hayasi, Y.; Kawanisi, M. Bull. Chem. Soc. Jpn. 1970, 43, 2506.
15. Hatjiarapoglou, L.; Spyroudis, S.; Varvoglis, A. J. Am. Chem. Soc. 1985, 107, 7178.
16. Hatjiarapoglou, L.; Varvoglis, A.; Alcock, N. W.; Pike, G. A. J. Chem. Soc., Perkin Trans. 1 1988, 2839.
17. Nicholas, J.; Hood, C.; Lloyd, D.; MacDonald, W. A.; Shepherd, T. M. Tetrahedron 1982, 38, 3355.
18. Beringer, F. M.; Huang, S. J. J. Org. Chem. 1964, 29, 445.
19. Beringer, F. M.; Huang, S. J. J. Org. Chem. 1964, 29, 1637.
20. Caserio, M. C.; Glusker, D. L.; Roberts, J. D. J. Am. Chem. Soc. 1959, 81, 336. For an excellent discussion of the radical pathway for diaryliodonium decomposition, see: Galli, C. Chem. Rev. 1988, 88, 765.
21. Scherrer, R. A.; Beatty, H. R. J. Org. Chem. 1980, 45, 2127. Cu(I) and Cu(II) may function in 2 → 3, 4a, b → 5a, b, and 6 → 7 in a chelation.
22. Callant, P.; Wilde, H. D.; Vandewalle, M. Tetrahedron 1981, 37, 2079.
23. Kondo, K.; Hiro, E.; Tunemoto, D. Tetrahedron Lett. 1976, 4489.