Chemistry of Oxaziridines. 1. Synthesis and Structure of 2-Arenesulfonyl-3-Aryloxaziridines. A New Class of Oxaziridines

Journal of the American Chemical Society

Volumn 102, Issue 6, 1980, Pages 2000-2005

  Davis, Franklin A ^a   Lamendola, Joseph ^a   Nadir, Upender ^a   Kluger, Edward W ^a   Sedergran, Thomas C ^a   Panunto, Thomas W ^a   Billmers, Robert ^a   Jenkins, Robert ^a   Turchi, Ignatius J ^a   Watson, William H ^b   Chen, Jenn Shyong ^b   Kimura, Michio ^b  

^a DREXEL UNIVERSITY   (United States)

^b TEXAS CHRISTIAN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001705553     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00526a040     Document Type: Article

References (46)

1. E. Schmitz, Adv. Heterocycl. Chem., 2, 83 (1963); 24, 63 (1979)
2. W. D. Emmons, Chem. Heterocycl. Compd., 19, 624 (1964).
3. M. Lemchen, “Mechanisms of Molecular Migrations”, Vol. 1, B. S. Thya-garajan, Ed., Wiley, New York, 1968, p 1.
4. F. A. Davis, U. K. Nadir, and E. W. Kluger, J. Chem. Soc., Chem. Commun., 25 (1977).
5. F. A. Davis, R. Jenkins, Jr., and S. G. Yocklovich, Tetrahedron Lett., 5171 (1978)
6. F. A. Davis, R. Jenkins, Jr., S. Q. A. Rlzvi, and T. W. Panunto, J. Chem. Soc., Chem. Commun., 600 (1979).
7. F. A. Davis, P. A. Mancinelli, K. Balasubramanian, and U. K. Nadir, J. Am. Chem. Soc., 101, 1044(1979).
8. F. A. Davis and U. K. Nadir, Tetrahedron Lett., 1721 (1977).
9. R. Albrecht, G. Kresze, and B. Mlakar, Chem. Ber., 97, 32 (1964).
10. F. A. Davis, W. A. R. Slegeir, S. Evans, A. Schwartz, D. L. Goff, and R. Palmer, J. Org. Chem., 38, 2809 (1973); F. A. Davis, A. J. Friedman, E. W. Kluger, E. B. Skibo, E. F. Fretz, A. P. Milicia, W. C. LeMasters, M. D. Bently, J. A. Lacadie, and I. B. Doublass, Chem. Ber., 42, 967 (1977).
11. F. A. Davis, A. J. Friedman, and E. W. Kluger, J. Am. Chem. Soc., 96, 5000 (1974)
12. F. A. Davis, A. J. Friedman, and U. K. Nadir, J. Am. Chem. Soc., 100,2844 (1978)
13. unpublished results.
14. F. A. Davis and P. A. Mancinelli, J. Org. Chem., 42, 389 (1977).
15. Adduot 8 is stable in chloroform-ethanol. However, in the presence of m-chlorobenzoic acid 8 slowly forms the ethyl sulfite ester (ArS(O)OEt).
16. L. Horner and E. Jurgens, Ber., 90, 2184 (1957)
17. W. D. Emmons, J. Am. Chem. Soc., 79, 5739 (1957).
18. R. A. Abramovitch, E. M. Smith, M. Humber, B. Purtschert, P. G. Srinivasan, and G. M. Singer, J. Chem. Soc., Perkin Trans. 1, 2589 (1974).
19. D. H. Aue and D. Thomas, J. Org. Chem., 39, 3855 (1974).
20. A. Padwa, J. Am. Chem. Soc., 87, 4365 (1965).
21. V. Madan and L. B. Clapp, J. Am. Chem. Soc., 91, 6087 (1969); 92, 4802 (1970).
22. Y. Ogata and Y. Sawaki, J. Am. Chem. Soc., 95, 4687, 4692 (1973)
23. M. Bucciarelli, A. Forni, I. Moretti, and G. Torre, J. Chem. Soc., Perkin Trans. 2, 1339 (1977)
24. A. Azman, J. Moller, and B. Plesnicar, J. Am. Chem. Soc., 101, 1107 (1979).
25. F. A. Davis and E. W. Kluger, J. Am. Chem. Soc., 98, 302 (1976).
26. J. M. Lehn, Fortschr. Chem. Forsch., 15, 311 (1970).
27. D. R. Boyd, W. B. Jennings, and R. Spratt, Chem. Commun., 745 (1970); C. Belzecki and D. Mostowicz, J. Org. Chem., 40, 3878 (1975); W. H. Pirkle and P. L. Rinaldi, Fortschr. Chem. Forsch., 42, 2080 (1977).
28. F. A. L. Anet, R. D. Trepka, and D. J. Cram, J. Am. Chem. Soc., 89, 357 (1967).
29. G. J. Jordan and D. R. Crist, Org. Magn. Reson., 9, 322 (1977).
30. H. P. Hamlow, S. Okuda, and N. Nakagawa, Tetrahedron Lett., 2553 (1964); F. Bohlmann, Ber., 91, 2157 (1958).
31. D. R. Boyd, R. Spratt, and D. M. Jerina, J. Chem. Soc. C, 2650 (1969).
32. D. M. Jerina, D. R. Boyd, L. Paolillo, and E. D. Becker, Tetrahedron Lett., 1483 (1970).
33. W. B. Jennings, D. R. Boyd, C. G. Watson, E. D. Becker, R. B. Bradley, and D. M. Jerina, J. Am. Chem. Soc., 94, 8501 (1972).
34. J. F. Cannon, J. Daly, J. V. Silverton, D. R. Boyd, and D. M. Jerina, J. Chem. Soc., Perkin Trans. 2, 1137 (1972).
35. Details of the X-ray structures of 9f and 9e have been reported. See: J. S. Chen, W. H. Watson, F. A. Davis, J. F. Lamendola, Jr., and U. K. Nadir, Acta Crystaiiogr., Sect. B, 34, 2861 (1978)
36. M. Kimura, W. H. Watson, F. A. Davis, J. F. Lamendola, Jr., and U. K. Nadir, Details of the X-ray structures of 9f and 9e have been reported., 35, 234 (1979).
37. B. Jerslev, Acta Crystaiiogr., 23, 645 (1967).
38. S. Pokrywiecki, C. M. Weeks, and W. L. Duax, Cryst. Struct. Commun., 2, 67 (1973).
39. T. Jordon, H. W. Smith, L. L. Lohr, and W. N. Lipscomb, J. Am. Chem. Soc., 85,846(1963).
40. For a discussion of a-sulfonyl carbanions see: E. Block, “Reactions of Organosulfur Compounds”, Academic Press, New York, 1978, Chapter 2.
41. S. Wolfe, A. Rauk, and I. G. Csizmadia, J. Am. Chem. Soc., 91, 1567 (1969).
42. J. S. Splitter and M. Calvin, J. Org. Chem., 30, 3427 (1965).
43. W. M. Jones and K. L. Krause, J. Am. Chem. Soc., 93, 551 (1971).
44. K. G. Taylor, S. R. Isaac, and J. L. Swigert, J. Org. Chem., 41, 1146 (1976).
45. R. W. Bost and G. F. Deebel, J. Elisha Mitchell Sci. Soc., 66, 157 (1950); Chem. Abstr., 46, 6049a (1952).
46. A. M. Grigorovskii, N. N. Dykhanov, and Z. M. Kimen, Zh. Obshch. Khim., 27, 531 (1957); Chem. Abstr., 51, 15526g(1957).