Foiled conjugation in α-oximino carbocations

Journal of Organic Chemistry

Volumn 61, Issue 10, 1996, Pages 3482-3489

  Creary, Xavier ^a   Jiang, Ziqi ^a  

^a UNIVERSITY OF NOTRE DAME   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001546154     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960073u     Document Type: Article

References (31)

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3. For examples of α-oximmo cations under nonsolvolytic conditions, see: (a) Shatzmiller, S.; Lidor, R.; Shalora, E.; Bahar, E.; J. Chem. Soc., Chem. Commun. 1984, 795. (b) Shatzmiller, S.; Shalom, E.; Bahar, E. J. Chem. Soc., Chem Commun. 1984, 1522. (c) Hansen, J. F.; Strong, S. A. J. Heterocycl. Chem 1977, 14, 1289. (d) Hansen, J. F.; Kim, Y. I.; McCrotty, S. E.; Strong, S. A.; Zimmer, D. E. Ibid. 1980, 17, 475.
4. For examples of α-oximmo cations under nonsolvolytic conditions, see: (a) Shatzmiller, S.; Lidor, R.; Shalora, E.; Bahar, E.; J. Chem. Soc., Chem. Commun. 1984, 795. (b) Shatzmiller, S.; Shalom, E.; Bahar, E. J. Chem. Soc., Chem Commun. 1984, 1522. (c) Hansen, J. F.; Strong, S. A. J. Heterocycl. Chem 1977, 14, 1289. (d) Hansen, J. F.; Kim, Y. I.; McCrotty, S. E.; Strong, S. A.; Zimmer, D. E. Ibid. 1980, 17, 475.
5. For examples of α-oximmo cations under nonsolvolytic conditions, see: (a) Shatzmiller, S.; Lidor, R.; Shalora, E.; Bahar, E.; J. Chem. Soc., Chem. Commun. 1984, 795. (b) Shatzmiller, S.; Shalom, E.; Bahar, E. J. Chem. Soc., Chem Commun. 1984, 1522. (c) Hansen, J. F.; Strong, S. A. J. Heterocycl. Chem 1977, 14, 1289. (d) Hansen, J. F.; Kim, Y. I.; McCrotty, S. E.; Strong, S. A.; Zimmer, D. E. Ibid. 1980, 17, 475.
6. For examples of α-oximmo cations under nonsolvolytic conditions, see: (a) Shatzmiller, S.; Lidor, R.; Shalora, E.; Bahar, E.; J. Chem. Soc., Chem. Commun. 1984, 795. (b) Shatzmiller, S.; Shalom, E.; Bahar, E. J. Chem. Soc., Chem Commun. 1984, 1522. (c) Hansen, J. F.; Strong, S. A. J. Heterocycl. Chem 1977, 14, 1289. (d) Hansen, J. F.; Kim, Y. I.; McCrotty, S. E.; Strong, S. A.; Zimmer, D. E. Ibid. 1980, 17, 475.
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11. 5 was measured for the 1-adamantyl system 17, and this value was used to calculate the rate of 19.
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18. An alternative approach to evaluating this effect is the calculation of hydride affinities. Relative hydride affinities of cations 4, 5, 6, and 24 are 0, 1.8, 6.6, and 15.2 kcal/mol, respectively, at the HF/6-31G* level.
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