Face Selectivity in the 1,3-Dipolar Cycloaddition Reactions of Benzonitrile Oxide with 5-Substituted Adamantane-2-thiones and 2-Methyleneadamantanes

Journal of Organic Chemistry

Volumn 62, Issue 14, 1997, Pages 4672-4676

  Chung, Wen Sheng ^a   Tsai, Tzong Liang ^a   Ho, Chia Chin ^a   Chiang, M Y N ^b   Le Noble, W J ^c  

^a NATIONAL CHIAO TUNG UNIVERSITY   (Taiwan)

^b NATIONAL SUN YAT SEN UNIVERSITY   (Taiwan)

^c STONY BROOK UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001198446     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9703717     Document Type: Article

References (29)

1. For reviews see: (a) Huisgen, R. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: New York, 1984; Vol. 1, pp 1-176. (b) Caramella, P.; Grünanger, P. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: New York, 1984; Vol. 1, pp 291-392. (c) Nitrite Oxides, Nitrones, and Nitronates in Organic Synthesis; Torssell, K. B. G., Ed.; VCH: New York, 1988. (d) Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon Press: Oxford, 1990; pp 269-367.
2. For reviews see: (a) Huisgen, R. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: New York, 1984; Vol. 1, pp 1-176. (b) Caramella, P.; Grünanger, P. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: New York, 1984; Vol. 1, pp 291-392. (c) Nitrite Oxides, Nitrones, and Nitronates in Organic Synthesis; Torssell, K. B. G., Ed.; VCH: New York, 1988. (d) Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon Press: Oxford, 1990; pp 269-367.
3. For reviews see: (a) Huisgen, R. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: New York, 1984; Vol. 1, pp 1-176. (b) Caramella, P.; Grünanger, P. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: New York, 1984; Vol. 1, pp 291-392. (c) Nitrite Oxides, Nitrones, and Nitronates in Organic Synthesis; Torssell, K. B. G., Ed.; VCH: New York, 1988. (d) Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon Press: Oxford, 1990; pp 269-367.
4. For reviews see: (a) Huisgen, R. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: New York, 1984; Vol. 1, pp 1-176. (b) Caramella, P.; Grünanger, P. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: New York, 1984; Vol. 1, pp 291-392. (c) Nitrite Oxides, Nitrones, and Nitronates in Organic Synthesis; Torssell, K. B. G., Ed.; VCH: New York, 1988. (d) Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon Press: Oxford, 1990; pp 269-367.
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22. All compounds mentioned in this paper have been completely characterized; see the Experimental Section. The final structural assignment of oxathiazolines was not straightforward. We were initially misled by the X-ray crystal structure of (Z)-5-Br, which crystallized from a 95:5 mixture of (E)-:(Z)-5-Br (due to poor separation). Fortunately, (Z)-5-F can be separated in pure form by means of column chromatography, and this finally revealed the fact that only the Z-form of oxathiazoline produced single crystals.
23. (a) Chung, W.-S.; Liu, Y.-D.; Wang, N.-J. J. Chem. Soc., Perkin Trans. 2 1995, 581.
24. (b) Chung, W.-S.; Turro, N. J.; Srivastava, S.; le Noble, W. J. J. Org. Chem. 1991, 56, 5020.
25. Srivastava, S.; Cheung, C.-K.; le Noble, W. J. Magn. Reson. Chem. 1985, 23, 232.
26. The HOMO energies for the dipolarophiles are as follows: 2 = -8.49 eV; 3 = -9.60 eV; 1 = -10.02 eV. Details of the energy and coefficient for frontier orbitals obtained by means of AM1 calculations will be published in a later paper. We thank Prof. J.-H. Yu of NTHU for the calculations.
27. Reichardt, C. Angew. Chem., Int. Ed. Engl. 1979, 18, 98.
28. Bonini, B. F.; MacCagnani, G.; Mazzanti, G.; Thijs, L.; Ambrosius, H. P. M. M.; Zwanenburg, B. J. Chem. Soc., Perkin Trans. 1 1977, 1468.
29. The author has deposited atomic coordinates for (Z)-5-F with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.