Reactions with Aziridines: 48. Friedel-Crafts Reactions with N-Sulfonated Aziridines and with Open-Chain Sulfonamides. Sulfonamides as Leaving Groups in Open-Chain Structures

Journal of Organic Chemistry

Volumn 54, Issue 1, 1989, Pages 193-199

  Stamm, Helmut ^a   Onistschenko, Andreas ^a   Buchholz, Berthold ^a   Mall, Thomas ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845183343     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00262a042     Document Type: Article

References (26)

1. Part 47: Stamm, H.; Speth, D. Arch. Pharm. (Weinheim) in the press. Part 46: Mall, T.; Stamm, H. Chem. Ber. 1988, 121, 1353–1355.
2. Ham. G. E. J. Org. Chem. 1964, 29. 3052–3055.
3. Buchholz. B.: Stamm. H. Isr. J. Chem. 1986. 27. 17–23.
4. Cited together with more recent papers in the following: Biggs, J.; Chapman, N. B.; Finch, A. F.; Wray, V. J. Chem. Soc. B 1971, 55–63.
5. Onistschenko, A.; Buchholz, B.; Stamm, H. Tetrahedron 1987,43, 565–576.
6. Compare also: Takeuchi, H.; Koyama, K. J. Chem. Soc., Perkin Trans. 2 1981, 121–126. However, some results are difficult to explain by the proposed mechanism, and the kinetic evidence (second order in MeCOacan perhaps be related with a dimerization of MeCO2H in cyclohexane. Activation by the weak acid MeCO2H needs further corroboration.
7. Genssler, W. J.; Rockett, J. C. J. Am. Chem. Soc. 1955, 77, 3262–3264. Genssler, W. J.; Kohler, W. R. J. Org. Chem. 1962, 27, 2754–2762. Genssler, W. J.; Dheer, S. K. J. Org. Chem. 1981, 46, 4051–4057.
8. Kurokawa, S.; Anderson, A. G., Jr. Bull. Chem. Soc. Jpn. 1983, 56, 2059–2064.
9. Beckhaus, H. D. ; Schaetzer, J.; Ruchardt, C. Tetrahedron Lett. 1983,24, 3307–3310. We thank Professor Christoph Ruchardt, Freiburg, for providing us with an authentic sample of 14P.
10. Olah, G. A.; Olah, J. A.; Okyama, T. J. Am. Chem. Soc. 1984,106, 5284–5290.
11. Heaney, H. In Comprehensive Organic Chemistry; Barton, D., Ollis, W. D., Stoddard J. F., Eds.; Pergamon Press: Oxford, 1979; Vol. 1.P 268–274.
12. Nakajima, T.; Suga, S.; Sugita, T.; Ichikawa, K. Tetrahedron 1969, 25, 1807–1816.
13. CN bond cleavage of N-substituted sulfonamides by boiling half-concentrated aqueous hydrochloric acid has been found (without alkyl transfer) for the N-substituents cinnamyl, 1-phenylallyl, 1-phenylpropyl, and tert-butyl but not for benzyl or allyl: Briscoe, P. A.; Challenger, F.; Duckworth, P. S. J. Chem. Soc. 1956, 1755–1768.
14. Arnett, E. W.; Wu, C. Y. J. Am. Chem. Soc. 1962, 84, 1680-1684
15. Virtanen, P. O. I.; Maikkula, M. Tetrahedron Lett. 1968, 4855–4858 and references cited therein.
16. Woods, C. W.; Borkovec, A. B.; Hart, F. M. J. Med. Chem. 1964, 7, 371–373.
17. Mall. T.: Stamm. H. J. Org. Chem. 1987. 52. 4812–4814.
18. Klötzer, W. Monatsh. Chem. 1970, 101, 1841–1850.
19. Stamm, H.; Sommer, A.; Woderer, A.; Wiesert, W.; Mall, T.; As-sithianakis, P. J. Ore. Chem. 1985, 50, 4946–4955.
20. Biltz, H. Justus Liebigs Ann. Chem. 1897, 296, 219–260.
21. Bodroux, F. Compt. Re nd. Hebd. Sceances Acad. Sci. 1901,132, 1333–1336.
22. Hauser, C. R.; Hamrick, P. J., Jr. J. Am. Chem. Soc. 1957, 79, 3142–3145.
23. Rogers, E. F.; Brown, H. D.; Rasmussen, I. M.; Heal, R. E. J. Am. Chem. Soc. 1953, 75, 2991–2999.
24. Markov, V. I.; Burmistrov, S. I. J. Gen. Chem. USSR 1965, 35, 153–157.
25. Johnson. T. B.: Guest. H. G. Am. Chem. J. 1909. 42. 340–353.
26. Peacock, D. H.; Dutta, U. C. J. Chem. Soc. 1934, 1303–1305.