Stereochemistry of the Electrophilic Homoallylic Chlorination Reaction of Sterically Congested Alkenes with Benzenesulfenyl Chloride: The Structure of the Phenylthiiranium Ion Intermediate

Journal of Organic Chemistry

Volumn 59, Issue 23, 1994, Pages 7108-7116

  Huang, Xicai ^a   Batchelor, Raymond J ^a   Einstein, Frederick W B ^a   Bennet, Andrew J ^a  

^a SIMON FRASER UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001663310     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00102a042     Document Type: Article

References (24)

1. Strating, J.; Wieringa, J. H.; Wynberg, H. J. Chem. Soc., Chem. Commun. 1969, 907-908.
2. Bennet, A. J.; Brown, R. S.; McClung, R. E. D.; Klobukowski, M.; Aarts, G. H. M.; Santarsiero, B. D.; Bellucci, G.; Bianchini, R. J. Am. Chem. Soc. 1991, 113, 8532-8534.
3. Brown, R. S.; Nagorski, R. W.; Bennet, A. J.; McClung, R. E. D.; Aarts, G. H. M.; Klobukowski, M.; McDonald, R.; Santarsiero, B. D. J. Am. Chem. Soc. 1994, 116, 2448-2456.
4. Slebocka-Tilk, H.; Ball, R. G.; Brown, R. S. J. Am. Chem. Soc. 1985, 107, 4504-4508.
5. Bolster, J.; Kellogg, R. M.; Meijer, E. W.; Wynberg, H. Tetrahedron Lett. 1979, 285-286.
6. Garrett, D. G. Tetrahedron Lett. 1979, 23, 285.
7. Lopez, L.; Troisi, L.; Mele, G. Tetrahedron Lett. 1991, 32, 117-120.
8. Meijer, E. W.; Kellogg, R. M.; Wynberg, H. J. Org. Chem. 1982, 47, 2005-2009.
9. Tolstikov, G. A.; Lerman, B. M.; Umanskaya, L. I.; Struchkov, Y. T. Izv. Akad. Nauk SSSR., Ser. Khim. 1982, 661-669.
10. Tolstikov, G. A.; Lerman, B. M.; Belogaeva, T. A. Izv. Akad. Nauk SSSR., Ser. Khim. 1986, 617-620.
11. Derome, A. E. Modern NMR Techniques for Chemistry Research; Pergamon: New York, 1987; pp 143-151.
12. Fleming, M. P.; McMurry, J. E. Organic Syntheses; Wiley: New York, 1990; Collect. Vol. VII, pp 1-4.
13. Hopkins, P. B.; Fuchs, P. L. J. Org. Chem. 1978, 43, 1208-1217.
14. Wieringa, J. H.; Strating, J.; Wynberg, H. Tetrahedron Lett. 1970, 4579-4582.
15. Lombardo, L. Org. Synth. 1987, 65, 81-89.
16. Busing, W. R.; Levy, H. A. Acta Crystallogr. 1957, 10, 180-182.
17. Prince, E. Mathematical Techniques in Crystallography and Materials Science; Springer-Verlag: New York: 1982; pp 79-82.
18. Gabe, E. J.; LePage, Y.; Charland, J-P.; Lee, F. L.; White, P. S. NRCVAX. An Interactive Program System for Structure Analysis. J. Appl. Cryst. 1989, 22, 384-387.
19. Watkin, D. J.; Carruthers, J. R.; Betteridge, P. W. CRYSTALS, Chemical Crystallography Laboratory, University of Oxford: Oxford, England, 1984.
20. International Tables for X-ray Crystallography; Kynoch Press: Birmingham, England, 1975, Vol. IV, pp 99-101.
21. Grant, D. M.; Cheney, B. V. J. Am. Chem. Soc. 1967, 89, 5315-5318.
22. Borodkin, G. I.; Gatilov, Yu.V.; Chernyak, E. I.; Shubin, V. G. Akad. Nauk SSSR, Bull. (Engl.) 1985, 34, 2622.
23. Hess, J.; Vos, A. Acta. Crystallogr., Sect. B 1977, 33, 3527-3530.
24. Watson, W. H.; Nagl, A. Acta. Crystallogr., Sect. C 1988, 44, 1627-1629.