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Volumn 63, Issue 25, 1998, Pages 9552-9554

Studies on the solvolytic reactivity of tertiary chloroalkanes in hexafluoro-2-propanol by ab initio and force field calculations

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE;

EID: 0032509387     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981089i     Document Type: Article
Times cited : (2)

References (30)
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    • Thesis, National Central University, Chung-Li, Taiwan, June
    • Hou, S.-J. M.S. Thesis, National Central University, Chung-Li, Taiwan, June, 1997.
    • (1997)
    • Hou, S.-J.M.S.1
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    • Wavefunction, Inc., 18401 Von Karman Ave., #370, Irvine, CA 92715
    • SPARTAN Version 4.1, Wavefunction, Inc., 18401 Von Karman Ave., #370, Irvine, CA 92715.
    • SPARTAN Version 4.1
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    • note
    • Our calculations for various conformations of chlorides 2 and 3 are consistent with those reported (ref 11). For the cation derived from 2, our result is also in harmony with the literature data (ref 15).
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    • A more recent work (Abboud, J.-L. M.; Castano, O.; Della, E. W.; Herreros, M.; Müller, P.; Notario, R.; Rossier, J.-C. J. Am. Chem. Soc. 1997, 119, 2262.) employing an elaborate method of gas-phase stability measurement and calculations at MP2/6-311G** level resulted in a larger slope (-0.492) and an excellent linear correlation between log k (solvolysis) against ΔG° for halide exchange in bridgehead carbocations.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 2262
    • Abboud, J.-L.M.1    Castano, O.2    Della, E.W.3    Herreros, M.4    Müller, P.5    Notario, R.6    Rossier, J.-C.7
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    • For examples, see: (a) Richard, J. P.; Amyes, T. L.; Ventor, T. J. Am. Chem. Soc. 1991, 113, 5871. (b) Richard, J. P.; Jagannadham, V.; Amyes, T. L.; Mishima, M.; Tsuno, Y. J. Am. Chem. Soc. 1994, 116, 6706.
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    • Liu, K.-T.1    Chang, L.-W.2    Chen, P.-S.3
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    • For examples, see: (a) Liu, K.-T.; Chang, L.-W.; Chen, P.-S. J. Org. Chem. 1992, 57, 5741. (b) Kevill, D. N.; D'Souza, M. J. J. Chem. Res., Synop. 1993, 174. (c) Takeuchi, K.; Ohga, Y.; Ushino, T.; Takasuka, M. J. Phys. Org. Chem. 1997, 10, 717.
    • (1993) J. Chem. Res., Synop. , pp. 174
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    • For examples, see: (a) Liu, K.-T.; Chang, L.-W.; Chen, P.-S. J. Org. Chem. 1992, 57, 5741. (b) Kevill, D. N.; D'Souza, M. J. J. Chem. Res., Synop. 1993, 174. (c) Takeuchi, K.; Ohga, Y.; Ushino, T.; Takasuka, M. J. Phys. Org. Chem. 1997, 10, 717.
    • (1997) J. Phys. Org. Chem. , vol.10 , pp. 717
    • Takeuchi, K.1    Ohga, Y.2    Ushino, T.3    Takasuka, M.4
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    • For example, an azide salt effect was observed for the solvolysis of tert-cumyl chloride in 90% acetone (Liu, K.-T.; Chen, P.-S.; Hu, C.-R.; Sheu, H.-C. J. Phys. Org. Chem. 1993, 6, 122) but not in 50% aqueous trifluoroethanol (ref 19a).
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    • Unpublished results from this laboratory
    • Unpublished results from this laboratory.
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    • note
    • It was found in a preliminary study that the same result was obtained by using purified and unpurified hexafluoro-2-propanol, respectively.


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