Primary vinyl cations in solution: Kinetics and products of β,β- disubstituted alkenyl(aryl)iodonium triflate fragmentations [17]

Journal of the American Chemical Society

Volumn 121, Issue 32, 1999, Pages 7437-7438

  Hinkle, Robert J ^b   McNeil, Anne J ^b   Thomas, Quinn A ^a,b   Andrews, Marie N ^b  

^a University of Southern Mississippi   (United States)

^b Dept of Economics and Thomas Jefferson Program in Public Policy at the College of William and Mary   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENYL GROUP; CATION; IODINE DERIVATIVE;

CHEMICAL STRUCTURE; GAS CHROMATOGRAPHY; KINETICS; LETTER; MASS SPECTROMETRY; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033581188     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9916310     Document Type: Letter

References (33)

1. For early work on the cubyl cation, see: (a) Moriarty, R. M.; Tuladhar, S. M.; Penmasta, R.; Awasthi, S. K. J. Am. Chem. Soc. 1990, 112, 3228-3230. (b) Eaton, P. E.; Yang, C.-X.; Xiong, Y. J. Am. Chem. Soc. 1990, 112, 3225- 3226. (c) Eaton, P. E.; Cunkle, G. T. Tetrahedron Lett. 1986, 6055-6058.
2. For early work on the cubyl cation, see: (a) Moriarty, R. M.; Tuladhar, S. M.; Penmasta, R.; Awasthi, S. K. J. Am. Chem. Soc. 1990, 112, 3228-3230. (b) Eaton, P. E.; Yang, C.-X.; Xiong, Y. J. Am. Chem. Soc. 1990, 112, 3225-3226. (c) Eaton, P. E.; Cunkle, G. T. Tetrahedron Lett. 1986, 6055-6058.
3. For early work on the cubyl cation, see: (a) Moriarty, R. M.; Tuladhar, S. M.; Penmasta, R.; Awasthi, S. K. J. Am. Chem. Soc. 1990, 112, 3228-3230. (b) Eaton, P. E.; Yang, C.-X.; Xiong, Y. J. Am. Chem. Soc. 1990, 112, 3225- 3226. (c) Eaton, P. E.; Cunkle, G. T. Tetrahedron Lett. 1986, 6055-6058.
4. Hypervalent iodine compounds in general have been the subject of several recent reviews and monographs: (a) Moriarty, R. M.; Prakash, O. In Advances in Heterocyclic Chemistry; Katritsky, A. R., Ed.; Academic: New York, 1998; pp 1-87. (b) Varvoglis, A. Tetrahedron 1997, 53, 1179-1255. (c) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 1996, 96, 1123-1178. (d) Varvoglis, A. Hypervalent Iodine in Organic Synthesis; Academic: New York, 1997.
5. Hypervalent iodine compounds in general have been the subject of several recent reviews and monographs: (a) Moriarty, R. M.; Prakash, O. In Advances in Heterocyclic Chemistry; Katritsky, A. R., Ed.; Academic: New York, 1998; pp 1-87. (b) Varvoglis, A. Tetrahedron 1997, 53, 1179-1255. (c) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 1996, 96, 1123-1178. (d) Varvoglis, A. Hypervalent Iodine in Organic Synthesis; Academic: New York, 1997.
6. Hypervalent iodine compounds in general have been the subject of several recent reviews and monographs: (a) Moriarty, R. M.; Prakash, O. In Advances in Heterocyclic Chemistry; Katritsky, A. R., Ed.; Academic: New York, 1998; pp 1-87. (b) Varvoglis, A. Tetrahedron 1997, 53, 1179-1255. (c) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 1996, 96, 1123-1178. (d) Varvoglis, A. Hypervalent Iodine in Organic Synthesis; Academic: New York, 1997.
7. Hypervalent iodine compounds in general have been the subject of several recent reviews and monographs: (a) Moriarty, R. M.; Prakash, O. In Advances in Heterocyclic Chemistry; Katritsky, A. R., Ed.; Academic: New York, 1998; pp 1-87. (b) Varvoglis, A. Tetrahedron 1997, 53, 1179-1255. (c) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 1996, 96, 1123-1178. (d) Varvoglis, A. Hypervalent Iodine in Organic Synthesis; Academic: New York, 1997.
8. Vinyl cations containing α-alkyl groups are a well-studied class of intermediates and are significantly more stable than those which do not contain the α-substituent. See, inter alia: (a) Kobayashi, S.; Hori, Y.; Hasako, T.; Koga, K.; Yamataka, H. J. Org. Chem. 1996, 61, 5274-5279. (b) Summerville, R. H.; Schleyer, P. v. R. J. Am. Chem. Soc. 1974, 96, 1110-1120. (d) Summerville, R. H.; Senkler, C. A.; Schleyer, P. v. R.; Dueber, T. E.; Stang, P. J. J. Am. Chem. Soc. 1974, 96, 1100-1109.
9. Vinyl cations containing α-alkyl groups are a well-studied class of intermediates and are significantly more stable than those which do not contain the α-substituent. See, inter alia: (a) Kobayashi, S.; Hori, Y.; Hasako, T.; Koga, K.; Yamataka, H. J. Org. Chem. 1996, 61, 5274-5279. (b) Summerville, R. H.; Schleyer, P. v. R. J. Am. Chem. Soc. 1974, 96, 1110-1120. (d) Summerville, R. H.; Senkler, C. A.; Schleyer, P. v. R.; Dueber, T. E.; Stang, P. J. J. Am. Chem. Soc. 1974, 96, 1100-1109.
10. Vinyl cations containing α-alkyl groups are a well-studied class of intermediates and are significantly more stable than those which do not contain the α-substituent. See, inter alia: (a) Kobayashi, S.; Hori, Y.; Hasako, T.; Koga, K.; Yamataka, H. J. Org. Chem. 1996, 61, 5274-5279. (b) Summerville, R. H.; Schleyer, P. v. R. J. Am. Chem. Soc. 1974, 96, 1110-1120. (d) Summerville, R. H.; Senkler, C. A.; Schleyer, P. v. R.; Dueber, T. E.; Stang, P. J. J. Am. Chem. Soc. 1974, 96, 1100-1109.
11. For NMR studies of stabilized vinyl cations, see: Siehl, H.-U. Pure Appl. Chem. 1995, 67, 769-775. Siehl, H.-U.; Kaufmann, F.-P.; Hori, K. J. Am. Chem. Soc. 1992, 114, 9343-9349.
12. For NMR studies of stabilized vinyl cations, see: Siehl, H.-U. Pure Appl. Chem. 1995, 67, 769-775. Siehl, H.-U.; Kaufmann, F.-P.; Hori, K. J. Am. Chem. Soc. 1992, 114, 9343-9349.
13. For a recent, comprehensive treatment of vinyl cation chemistry, see: Dicoordinated Carbocations; Rappoport, Z., Stang, P. J., Eds.; John Wiley and Sons: New York, 1997.
14. Kang, S.-K.; Ho, P.-S.; Yoon, S.-K.; Lee, J. -C.; Lee, K.-J. Synthesis 1998, 823-825; Ryan, J. H.; Stang, P. J. J. Org. Chem. 1996, 61, 6162- 6165; Hinkle, R. J.; Poulter, G. M.; Stang, P. J. J. Am. Chem. Soc. 1993, 115, 11626-11627; Moriarty, R. M.; Epa, W. R. Tetrahedron Lett. 1992, 4095- 4098.
15. Kang, S.-K.; Ho, P.-S.; Yoon, S.-K.; Lee, J. -C.; Lee, K.-J. Synthesis 1998, 823-825; Ryan, J. H.; Stang, P. J. J. Org. Chem. 1996, 61, 6162-6165; Hinkle, R. J.; Poulter, G. M.; Stang, P. J. J. Am. Chem. Soc. 1993, 115, 11626-11627; Moriarty, R. M.; Epa, W. R. Tetrahedron Lett. 1992, 4095- 4098.
16. Kang, S.-K.; Ho, P.-S.; Yoon, S.-K.; Lee, J. -C.; Lee, K.-J. Synthesis 1998, 823-825; Ryan, J. H.; Stang, P. J. J. Org. Chem. 1996, 61, 6162- 6165; Hinkle, R. J.; Poulter, G. M.; Stang, P. J. J. Am. Chem. Soc. 1993, 115, 11626-11627; Moriarty, R. M.; Epa, W. R. Tetrahedron Lett. 1992, 4095- 4098.
17. Kang, S.-K.; Ho, P.-S.; Yoon, S.-K.; Lee, J. -C.; Lee, K.-J. Synthesis 1998, 823-825; Ryan, J. H.; Stang, P. J. J. Org. Chem. 1996, 61, 6162- 6165; Hinkle, R. J.; Poulter, G. M.; Stang, P. J. J. Am. Chem. Soc. 1993, 115, 11626-11627; Moriarty, R. M.; Epa, W. R. Tetrahedron Lett. 1992, 4095-4098.
18. Moriarty, R. M.; Epa, W. R.; Awasthi, A. K. J. Am. Chem. Soc. 1991, 113, 6315-6316.
19. Ochiai, M.; Shu, T.; Nagaoka, T.; Kitagawa, Y. J. Org. Chem. 1997, 62, 2130-2138.
20. Ochiai, M.; Sumi, K.; Takaoka, Y.; Kunishima, M.; Nagao, Y.; Shiro, M.; Fujita, E. Tetrahedron 1988, 4095-4112.
21. Okuyama, T.; Takino, T.; Sueda, T.; Ochiai, M. J. Am. Chem. Soc. 1995, 117, 3360-3367.
22. For a report showing decomposition of an iodonium salt via a phenonium ion, see: Hinkle, R. J.; Thomas, D. B. J. Org. Chem. 1997, 62, 7534-7535.
23. A second β-methyl group stabilizes the primary vinyl cation by 24.0 kcal/mol (MP3/6-31G*//6-31G*). See ref 6, p 34.
24. While the current work was in progress, Okuyama and co-workers described rearrangements of less-reactive disubstituted alkenyl(phenyl)-iodonium salts. Okuyama, T.; Sato, K.; Ochiai, M. Chem. Lett. 1998, 1177-1178.
25. Hinkle, R. J.; Stang, P. J. Synthesis 1994, 393-396. Zhdankin, V. V.; Scheuller, M. C.; Stang, P. J. Tetrahedron Lett. 1993, 34, 6853-6856.
26. Hinkle, R. J.; Stang, P. J. Synthesis 1994, 393-396. Zhdankin, V. V.; Scheuller, M. C.; Stang, P. J. Tetrahedron Lett. 1993, 34, 6853-6856.
27. Enol triflates were synthesized according to standard procedures by means of the hindered base method and the appropriate ketone or aldehyde: Stang, P. J.; Treptow, W. Synthesis 1980, 283-284.
28. N2 reactions are documented for simple alkylvinyl(phenyl)-iodonium salts: (a) Okuyama, T.; Takino, T.; Sago, K.; Ochiai, M. J. Am. Chem. Soc. 1998, 120, 2275-2282. (b) Okuyama, T.; Takino, T.; Sato, K.; Oshima, K. Imamura, S.; Yamataka, H.; Asano, T.; Ochiai, M. Bull. Chem. Soc. Jpn. 1998, 71, 243-257. (c) Ochiai, M.; Ochima, K.; Masaki, Y. J. Am. Chem. Soc. 1991, 113, 7059-7061.
29. N2 reactions are documented for simple alkylvinyl(phenyl)- iodonium salts: (a) Okuyama, T.; Takino, T.; Sago, K.; Ochiai, M. J. Am. Chem. Soc. 1998, 120, 2275-2282. (b) Okuyama, T.; Takino, T.; Sato, K.; Oshima, K. Imamura, S.; Yamataka, H.; Asano, T.; Ochiai, M. Bull. Chem. Soc. Jpn. 1998, 71, 243-257. (c) Ochiai, M.; Ochima, K.; Masaki, Y. J. Am. Chem. Soc. 1991, 113, 7059-7061.
30. N2 reactions are documented for simple alkylvinyl(phenyl)- iodonium salts: (a) Okuyama, T.; Takino, T.; Sago, K.; Ochiai, M. J. Am. Chem. Soc. 1998, 120, 2275-2282. (b) Okuyama, T.; Takino, T.; Sato, K.; Oshima, K. Imamura, S.; Yamataka, H.; Asano, T.; Ochiai, M. Bull. Chem. Soc. Jpn. 1998, 71, 243-257. (c) Ochiai, M.; Ochima, K.; Masaki, Y. J. Am. Chem. Soc. 1991, 113, 7059-7061.
31. N-E reactions was recently published: Lucchini, V.; Modena, G.; Pasquato, L. J. Am. Chem. Soc. 1995, 117, 2297-2300.
32. An addition-elimination pathway is proposed for salts containing a β-phenylsulfonyl moiety: Ochiai, M.; Oshima, K.; Masaki, Y. Tetrahedron Lett. 1991, 32, 7711-7714.
33. When multiple substituents are contained in the same aromatic ring, the σ-values are additive. Hammet, L. P.; Physical Organic Chemistry, 2nd ed.; McGraw-Hill: New York, 1970; p 367.