Cycloaddition reactions of 1-phenylseleno-2-(p-toluenesulfonyl)ethyne

Journal of Organic Chemistry

Volumn 64, Issue 20, 1999, Pages 7426-7432

  Back, Thomas G ^a   Bethell, Richard J ^a   Parvez, Masood ^a   Taylor, Jerry A ^a   Wehrli, Daniel ^a  

^a UNIVERSITY OF CALGARY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 BUTADIENE; ACETYLENE; AZIDE; BENZONITRILE; BETA PINENE; DIAZOMETHANE; ISOXAZOLE DERIVATIVE; KETENE DERIVATIVE; SELENIDE; TOLUENE; TRIAZOLE DERIVATIVE; TRIMETHYLSILYL DERIVATIVE;

AROMATIZATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CONTROLLED STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; REACTION ANALYSIS;

EID: 0033215411     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990730t     Document Type: Article

References (57)

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5. (e) Tanaka, K.; Kaji, A. In The Chemistry of Sulphones and Sulphoxides; Patai, S., Rappoport, Z., Stirling, C. J. M., Eds.; Wiley: Chichester, 1988; Chapter 15.
6. For examples, see ref 1a, Chapters 2 and 6. Also see: (a) De Lucchi, O.; Pasquato, L. Tetrahedron 1988, 44, 6755. (b) Paquette, L. A.; Williams, R. V. Tetrahedron Lett. 1981, 22, 4643. (c) Williams, R. V.; Chauhan, K.; Gadgil, V. R. J. Chem. Soc., Chem. Commun. 1994, 1739. (d) Hickey, E. R.; Paquette, L. A. J. Am. Chem. Soc. 1995, 117, 163. (e) Pasquato, L.; De Lucchi, O.; Krotz, L. Tetrahedron Lett. 1991, 32, 2177. (f) Corey, E. J.; Da Silva Jardine, P.; Mohri, T. Tetrahedron Lett. 1988, 29, 6409. (g) Kotian, P. L.; Carroll, F. I. Synth. Commun. 1995, 25, 63. (h) Davis, A. P.; Whitham, G. H. J. Chem. Soc., Chem. Commun. 1980, 639. (i) Huang, D. F.; Shen, T. Y. Tetrahedron Lett. 1993, 34, 4477. (j) Jones, C. D.; Simpkins, N. S.; Giblin, G. M. P. Tetrahedron Lett. 1998, 39, 1021 and 1023. (k) Clasby, M. C.; Craig, D.; Marsh, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1444. (l) Virgili, M.; Belloch, J.; Moyano, A.; Pericàs, M. A.; Riera, A. Tetrahedron Lett. 1991, 32, 4583. (m) Djeghaba, Z.; Jousseaume, B.; Ratier, M.; Duboudin, J.-G. J. Organomet. Chem. 1986, 304, 115.
7. For examples, see ref 1a, Chapters 2 and 6. Also see: (a) De Lucchi, O.; Pasquato, L. Tetrahedron 1988, 44, 6755. (b) Paquette, L. A.; Williams, R. V. Tetrahedron Lett. 1981, 22, 4643. (c) Williams, R. V.; Chauhan, K.; Gadgil, V. R. J. Chem. Soc., Chem. Commun. 1994, 1739. (d) Hickey, E. R.; Paquette, L. A. J. Am. Chem. Soc. 1995, 117, 163. (e) Pasquato, L.; De Lucchi, O.; Krotz, L. Tetrahedron Lett. 1991, 32, 2177. (f) Corey, E. J.; Da Silva Jardine, P.; Mohri, T. Tetrahedron Lett. 1988, 29, 6409. (g) Kotian, P. L.; Carroll, F. I. Synth. Commun. 1995, 25, 63. (h) Davis, A. P.; Whitham, G. H. J. Chem. Soc., Chem. Commun. 1980, 639. (i) Huang, D. F.; Shen, T. Y. Tetrahedron Lett. 1993, 34, 4477. (j) Jones, C. D.; Simpkins, N. S.; Giblin, G. M. P. Tetrahedron Lett. 1998, 39, 1021 and 1023. (k) Clasby, M. C.; Craig, D.; Marsh, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1444. (l) Virgili, M.; Belloch, J.; Moyano, A.; Pericàs, M. A.; Riera, A. Tetrahedron Lett. 1991, 32, 4583. (m) Djeghaba, Z.; Jousseaume, B.; Ratier, M.; Duboudin, J.-G. J. Organomet. Chem. 1986, 304, 115.
8. For examples, see ref 1a, Chapters 2 and 6. Also see: (a) De Lucchi, O.; Pasquato, L. Tetrahedron 1988, 44, 6755. (b) Paquette, L. A.; Williams, R. V. Tetrahedron Lett. 1981, 22, 4643. (c) Williams, R. V.; Chauhan, K.; Gadgil, V. R. J. Chem. Soc., Chem. Commun. 1994, 1739. (d) Hickey, E. R.; Paquette, L. A. J. Am. Chem. Soc. 1995, 117, 163. (e) Pasquato, L.; De Lucchi, O.; Krotz, L. Tetrahedron Lett. 1991, 32, 2177. (f) Corey, E. J.; Da Silva Jardine, P.; Mohri, T. Tetrahedron Lett. 1988, 29, 6409. (g) Kotian, P. L.; Carroll, F. I. Synth. Commun. 1995, 25, 63. (h) Davis, A. P.; Whitham, G. H. J. Chem. Soc., Chem. Commun. 1980, 639. (i) Huang, D. F.; Shen, T. Y. Tetrahedron Lett. 1993, 34, 4477. (j) Jones, C. D.; Simpkins, N. S.; Giblin, G. M. P. Tetrahedron Lett. 1998, 39, 1021 and 1023. (k) Clasby, M. C.; Craig, D.; Marsh, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1444. (l) Virgili, M.; Belloch, J.; Moyano, A.; Pericàs, M. A.; Riera, A. Tetrahedron Lett. 1991, 32, 4583. (m) Djeghaba, Z.; Jousseaume, B.; Ratier, M.; Duboudin, J.-G. J. Organomet. Chem. 1986, 304, 115.
9. For examples, see ref 1a, Chapters 2 and 6. Also see: (a) De Lucchi, O.; Pasquato, L. Tetrahedron 1988, 44, 6755. (b) Paquette, L. A.; Williams, R. V. Tetrahedron Lett. 1981, 22, 4643. (c) Williams, R. V.; Chauhan, K.; Gadgil, V. R. J. Chem. Soc., Chem. Commun. 1994, 1739. (d) Hickey, E. R.; Paquette, L. A. J. Am. Chem. Soc. 1995, 117, 163. (e) Pasquato, L.; De Lucchi, O.; Krotz, L. Tetrahedron Lett. 1991, 32, 2177. (f) Corey, E. J.; Da Silva Jardine, P.; Mohri, T. Tetrahedron Lett. 1988, 29, 6409. (g) Kotian, P. L.; Carroll, F. I. Synth. Commun. 1995, 25, 63. (h) Davis, A. P.; Whitham, G. H. J. Chem. Soc., Chem. Commun. 1980, 639. (i) Huang, D. F.; Shen, T. Y. Tetrahedron Lett. 1993, 34, 4477. (j) Jones, C. D.; Simpkins, N. S.; Giblin, G. M. P. Tetrahedron Lett. 1998, 39, 1021 and 1023. (k) Clasby, M. C.; Craig, D.; Marsh, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1444. (l) Virgili, M.; Belloch, J.; Moyano, A.; Pericàs, M. A.; Riera, A. Tetrahedron Lett. 1991, 32, 4583. (m) Djeghaba, Z.; Jousseaume, B.; Ratier, M.; Duboudin, J.-G. J. Organomet. Chem. 1986, 304, 115.
10. For examples, see ref 1a, Chapters 2 and 6. Also see: (a) De Lucchi, O.; Pasquato, L. Tetrahedron 1988, 44, 6755. (b) Paquette, L. A.; Williams, R. V. Tetrahedron Lett. 1981, 22, 4643. (c) Williams, R. V.; Chauhan, K.; Gadgil, V. R. J. Chem. Soc., Chem. Commun. 1994, 1739. (d) Hickey, E. R.; Paquette, L. A. J. Am. Chem. Soc. 1995, 117, 163. (e) Pasquato, L.; De Lucchi, O.; Krotz, L. Tetrahedron Lett. 1991, 32, 2177. (f) Corey, E. J.; Da Silva Jardine, P.; Mohri, T. Tetrahedron Lett. 1988, 29, 6409. (g) Kotian, P. L.; Carroll, F. I. Synth. Commun. 1995, 25, 63. (h) Davis, A. P.; Whitham, G. H. J. Chem. Soc., Chem. Commun. 1980, 639. (i) Huang, D. F.; Shen, T. Y. Tetrahedron Lett. 1993, 34, 4477. (j) Jones, C. D.; Simpkins, N. S.; Giblin, G. M. P. Tetrahedron Lett. 1998, 39, 1021 and 1023. (k) Clasby, M. C.; Craig, D.; Marsh, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1444. (l) Virgili, M.; Belloch, J.; Moyano, A.; Pericàs, M. A.; Riera, A. Tetrahedron Lett. 1991, 32, 4583. (m) Djeghaba, Z.; Jousseaume, B.; Ratier, M.; Duboudin, J.-G. J. Organomet. Chem. 1986, 304, 115.
11. For examples, see ref 1a, Chapters 2 and 6. Also see: (a) De Lucchi, O.; Pasquato, L. Tetrahedron 1988, 44, 6755. (b) Paquette, L. A.; Williams, R. V. Tetrahedron Lett. 1981, 22, 4643. (c) Williams, R. V.; Chauhan, K.; Gadgil, V. R. J. Chem. Soc., Chem. Commun. 1994, 1739. (d) Hickey, E. R.; Paquette, L. A. J. Am. Chem. Soc. 1995, 117, 163. (e) Pasquato, L.; De Lucchi, O.; Krotz, L. Tetrahedron Lett. 1991, 32, 2177. (f) Corey, E. J.; Da Silva Jardine, P.; Mohri, T. Tetrahedron Lett. 1988, 29, 6409. (g) Kotian, P. L.; Carroll, F. I. Synth. Commun. 1995, 25, 63. (h) Davis, A. P.; Whitham, G. H. J. Chem. Soc., Chem. Commun. 1980, 639. (i) Huang, D. F.; Shen, T. Y. Tetrahedron Lett. 1993, 34, 4477. (j) Jones, C. D.; Simpkins, N. S.; Giblin, G. M. P. Tetrahedron Lett. 1998, 39, 1021 and 1023. (k) Clasby, M. C.; Craig, D.; Marsh, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1444. (l) Virgili, M.; Belloch, J.; Moyano, A.; Pericàs, M. A.; Riera, A. Tetrahedron Lett. 1991, 32, 4583. (m) Djeghaba, Z.; Jousseaume, B.; Ratier, M.; Duboudin, J.-G. J. Organomet. Chem. 1986, 304, 115.
12. For examples, see ref 1a, Chapters 2 and 6. Also see: (a) De Lucchi, O.; Pasquato, L. Tetrahedron 1988, 44, 6755. (b) Paquette, L. A.; Williams, R. V. Tetrahedron Lett. 1981, 22, 4643. (c) Williams, R. V.; Chauhan, K.; Gadgil, V. R. J. Chem. Soc., Chem. Commun. 1994, 1739. (d) Hickey, E. R.; Paquette, L. A. J. Am. Chem. Soc. 1995, 117, 163. (e) Pasquato, L.; De Lucchi, O.; Krotz, L. Tetrahedron Lett. 1991, 32, 2177. (f) Corey, E. J.; Da Silva Jardine, P.; Mohri, T. Tetrahedron Lett. 1988, 29, 6409. (g) Kotian, P. L.; Carroll, F. I. Synth. Commun. 1995, 25, 63. (h) Davis, A. P.; Whitham, G. H. J. Chem. Soc., Chem. Commun. 1980, 639. (i) Huang, D. F.; Shen, T. Y. Tetrahedron Lett. 1993, 34, 4477. (j) Jones, C. D.; Simpkins, N. S.; Giblin, G. M. P. Tetrahedron Lett. 1998, 39, 1021 and 1023. (k) Clasby, M. C.; Craig, D.; Marsh, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1444. (l) Virgili, M.; Belloch, J.; Moyano, A.; Pericàs, M. A.; Riera, A. Tetrahedron Lett. 1991, 32, 4583. (m) Djeghaba, Z.; Jousseaume, B.; Ratier, M.; Duboudin, J.-G. J. Organomet. Chem. 1986, 304, 115.
13. For examples, see ref 1a, Chapters 2 and 6. Also see: (a) De Lucchi, O.; Pasquato, L. Tetrahedron 1988, 44, 6755. (b) Paquette, L. A.; Williams, R. V. Tetrahedron Lett. 1981, 22, 4643. (c) Williams, R. V.; Chauhan, K.; Gadgil, V. R. J. Chem. Soc., Chem. Commun. 1994, 1739. (d) Hickey, E. R.; Paquette, L. A. J. Am. Chem. Soc. 1995, 117, 163. (e) Pasquato, L.; De Lucchi, O.; Krotz, L. Tetrahedron Lett. 1991, 32, 2177. (f) Corey, E. J.; Da Silva Jardine, P.; Mohri, T. Tetrahedron Lett. 1988, 29, 6409. (g) Kotian, P. L.; Carroll, F. I. Synth. Commun. 1995, 25, 63. (h) Davis, A. P.; Whitham, G. H. J. Chem. Soc., Chem. Commun. 1980, 639. (i) Huang, D. F.; Shen, T. Y. Tetrahedron Lett. 1993, 34, 4477. (j) Jones, C. D.; Simpkins, N. S.; Giblin, G. M. P. Tetrahedron Lett. 1998, 39, 1021 and 1023. (k) Clasby, M. C.; Craig, D.; Marsh, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1444. (l) Virgili, M.; Belloch, J.; Moyano, A.; Pericàs, M. A.; Riera, A. Tetrahedron Lett. 1991, 32, 4583. (m) Djeghaba, Z.; Jousseaume, B.; Ratier, M.; Duboudin, J.-G. J. Organomet. Chem. 1986, 304, 115.
14. For examples, see ref 1a, Chapters 2 and 6. Also see: (a) De Lucchi, O.; Pasquato, L. Tetrahedron 1988, 44, 6755. (b) Paquette, L. A.; Williams, R. V. Tetrahedron Lett. 1981, 22, 4643. (c) Williams, R. V.; Chauhan, K.; Gadgil, V. R. J. Chem. Soc., Chem. Commun. 1994, 1739. (d) Hickey, E. R.; Paquette, L. A. J. Am. Chem. Soc. 1995, 117, 163. (e) Pasquato, L.; De Lucchi, O.; Krotz, L. Tetrahedron Lett. 1991, 32, 2177. (f) Corey, E. J.; Da Silva Jardine, P.; Mohri, T. Tetrahedron Lett. 1988, 29, 6409. (g) Kotian, P. L.; Carroll, F. I. Synth. Commun. 1995, 25, 63. (h) Davis, A. P.; Whitham, G. H. J. Chem. Soc., Chem. Commun. 1980, 639. (i) Huang, D. F.; Shen, T. Y. Tetrahedron Lett. 1993, 34, 4477. (j) Jones, C. D.; Simpkins, N. S.; Giblin, G. M. P. Tetrahedron Lett. 1998, 39, 1021 and 1023. (k) Clasby, M. C.; Craig, D.; Marsh, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1444. (l) Virgili, M.; Belloch, J.; Moyano, A.; Pericàs, M. A.; Riera, A. Tetrahedron Lett. 1991, 32, 4583. (m) Djeghaba, Z.; Jousseaume, B.; Ratier, M.; Duboudin, J.-G. J. Organomet. Chem. 1986, 304, 115.
15. For examples, see ref 1a, Chapters 2 and 6. Also see: (a) De Lucchi, O.; Pasquato, L. Tetrahedron 1988, 44, 6755. (b) Paquette, L. A.; Williams, R. V. Tetrahedron Lett. 1981, 22, 4643. (c) Williams, R. V.; Chauhan, K.; Gadgil, V. R. J. Chem. Soc., Chem. Commun. 1994, 1739. (d) Hickey, E. R.; Paquette, L. A. J. Am. Chem. Soc. 1995, 117, 163. (e) Pasquato, L.; De Lucchi, O.; Krotz, L. Tetrahedron Lett. 1991, 32, 2177. (f) Corey, E. J.; Da Silva Jardine, P.; Mohri, T. Tetrahedron Lett. 1988, 29, 6409. (g) Kotian, P. L.; Carroll, F. I. Synth. Commun. 1995, 25, 63. (h) Davis, A. P.; Whitham, G. H. J. Chem. Soc., Chem. Commun. 1980, 639. (i) Huang, D. F.; Shen, T. Y. Tetrahedron Lett. 1993, 34, 4477. (j) Jones, C. D.; Simpkins, N. S.; Giblin, G. M. P. Tetrahedron Lett. 1998, 39, 1021 and 1023. (k) Clasby, M. C.; Craig, D.; Marsh, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1444. (l) Virgili, M.; Belloch, J.; Moyano, A.; Pericàs, M. A.; Riera, A. Tetrahedron Lett. 1991, 32, 4583. (m) Djeghaba, Z.; Jousseaume, B.; Ratier, M.; Duboudin, J.-G. J. Organomet. Chem. 1986, 304, 115.
16. For examples, see ref 1a, Chapters 2 and 6. Also see: (a) De Lucchi, O.; Pasquato, L. Tetrahedron 1988, 44, 6755. (b) Paquette, L. A.; Williams, R. V. Tetrahedron Lett. 1981, 22, 4643. (c) Williams, R. V.; Chauhan, K.; Gadgil, V. R. J. Chem. Soc., Chem. Commun. 1994, 1739. (d) Hickey, E. R.; Paquette, L. A. J. Am. Chem. Soc. 1995, 117, 163. (e) Pasquato, L.; De Lucchi, O.; Krotz, L. Tetrahedron Lett. 1991, 32, 2177. (f) Corey, E. J.; Da Silva Jardine, P.; Mohri, T. Tetrahedron Lett. 1988, 29, 6409. (g) Kotian, P. L.; Carroll, F. I. Synth. Commun. 1995, 25, 63. (h) Davis, A. P.; Whitham, G. H. J. Chem. Soc., Chem. Commun. 1980, 639. (i) Huang, D. F.; Shen, T. Y. Tetrahedron Lett. 1993, 34, 4477. (j) Jones, C. D.; Simpkins, N. S.; Giblin, G. M. P. Tetrahedron Lett. 1998, 39, 1021 and 1023. (k) Clasby, M. C.; Craig, D.; Marsh, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1444. (l) Virgili, M.; Belloch, J.; Moyano, A.; Pericàs, M. A.; Riera, A. Tetrahedron Lett. 1991, 32, 4583. (m) Djeghaba, Z.; Jousseaume, B.; Ratier, M.; Duboudin, J.-G. J. Organomet. Chem. 1986, 304, 115.
17. For examples, see ref 1a, Chapters 2 and 6. Also see: (a) De Lucchi, O.; Pasquato, L. Tetrahedron 1988, 44, 6755. (b) Paquette, L. A.; Williams, R. V. Tetrahedron Lett. 1981, 22, 4643. (c) Williams, R. V.; Chauhan, K.; Gadgil, V. R. J. Chem. Soc., Chem. Commun. 1994, 1739. (d) Hickey, E. R.; Paquette, L. A. J. Am. Chem. Soc. 1995, 117, 163. (e) Pasquato, L.; De Lucchi, O.; Krotz, L. Tetrahedron Lett. 1991, 32, 2177. (f) Corey, E. J.; Da Silva Jardine, P.; Mohri, T. Tetrahedron Lett. 1988, 29, 6409. (g) Kotian, P. L.; Carroll, F. I. Synth. Commun. 1995, 25, 63. (h) Davis, A. P.; Whitham, G. H. J. Chem. Soc., Chem. Commun. 1980, 639. (i) Huang, D. F.; Shen, T. Y. Tetrahedron Lett. 1993, 34, 4477. (j) Jones, C. D.; Simpkins, N. S.; Giblin, G. M. P. Tetrahedron Lett. 1998, 39, 1021 and 1023. (k) Clasby, M. C.; Craig, D.; Marsh, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1444. (l) Virgili, M.; Belloch, J.; Moyano, A.; Pericàs, M. A.; Riera, A. Tetrahedron Lett. 1991, 32, 4583. (m) Djeghaba, Z.; Jousseaume, B.; Ratier, M.; Duboudin, J.-G. J. Organomet. Chem. 1986, 304, 115.
18. For examples, see ref 1a, Chapters 2 and 6. Also see: (a) De Lucchi, O.; Pasquato, L. Tetrahedron 1988, 44, 6755. (b) Paquette, L. A.; Williams, R. V. Tetrahedron Lett. 1981, 22, 4643. (c) Williams, R. V.; Chauhan, K.; Gadgil, V. R. J. Chem. Soc., Chem. Commun. 1994, 1739. (d) Hickey, E. R.; Paquette, L. A. J. Am. Chem. Soc. 1995, 117, 163. (e) Pasquato, L.; De Lucchi, O.; Krotz, L. Tetrahedron Lett. 1991, 32, 2177. (f) Corey, E. J.; Da Silva Jardine, P.; Mohri, T. Tetrahedron Lett. 1988, 29, 6409. (g) Kotian, P. L.; Carroll, F. I. Synth. Commun. 1995, 25, 63. (h) Davis, A. P.; Whitham, G. H. J. Chem. Soc., Chem. Commun. 1980, 639. (i) Huang, D. F.; Shen, T. Y. Tetrahedron Lett. 1993, 34, 4477. (j) Jones, C. D.; Simpkins, N. S.; Giblin, G. M. P. Tetrahedron Lett. 1998, 39, 1021 and 1023. (k) Clasby, M. C.; Craig, D.; Marsh, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1444. (l) Virgili, M.; Belloch, J.; Moyano, A.; Pericàs, M. A.; Riera, A. Tetrahedron Lett. 1991, 32, 4583. (m) Djeghaba, Z.; Jousseaume, B.; Ratier, M.; Duboudin, J.-G. J. Organomet. Chem. 1986, 304, 115.
19. Reference 1a, Chapter 9 and references therein.
20. For a recent review, see: Stang, P. J.; Zhdankin, V. V. In Comprehensive Organic Functional Group Transformations; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Eds.; Elsevier: Oxford, 1995; Vol. 2, Chapter 2.21.
21. (a) Back, T. G.; Wehrli, D. Tetrahedron Lett. 1995, 36, 4737.
22. (b) Back, T. G.; Bethell, R. J.; Parvez, M.; Wehrli, D. J. Org. Chem. 1998, 63, 7908.
23. (c) Compound 1 was also recently reported as an intermediate in the reaction of tosylalkynyliodonium triflate with benzeneselenolate: Stang, P. J.; Murch, P. Synthesis 1997, 1378.
24. Preliminary communication: Back, T. G.; Wehrli, D. Synlett 1995, 1123. This work is largely based on the Ph.D. Thesis of D. Wehrli (University of Calgary, 1997).
25. Fleming, I. Frontier Orbitals and Organic Chemical Reactions; Wiley: Chichester, 1976.
26. If 1 acts as the dienophile in a Diels-Alder cycloaddition with normal electron demand, then the frontier orbital interaction that determines the regiochemistry is between the LUMO of 1 and the HOMO of the diene. We noted earlier (ref 5b) that the LUMO of 1 is distributed roughly evenly over the two acetylenic carbon atoms, in contrast to what is expected in a simple acetylenic sulfone, where the β-carbon atom of the LUMO normally possesses the larger coefficient. Thus, it appears that the selenide substituent significantly affects the LUMO of 1 and therefore plays a major role in determining the regiochemistry of the cycloadditions and conjugate additons of 1.
27. It has been pointed out that hetero-Diels-Alder reactions between an α,β-unsaturated aldehyde and an electron-rich dienophile can proceed with inverse electron demand: (a) Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon Press: Oxford, 1990; pp 40-45. (b) Desimoni, G.; Tacconi, G. Chem. Rev. 1975, 75, 651.
28. It has been pointed out that hetero-Diels-Alder reactions between an α,β-unsaturated aldehyde and an electron-rich dienophile can proceed with inverse electron demand: (a) Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon Press: Oxford, 1990; pp 40-45. (b) Desimoni, G.; Tacconi, G. Chem. Rev. 1975, 75, 651.
29. It is possible that 1 is capable of cycloadditions with either normal or inverse electron demand, depending upon whether the other reactant is electron-rich or electron-poor. It is interesting to note that 2-sulfonyl-1,3-dienes also display dual electron demand in cycloaddi-tions and thus react with both electron-rich and electron-deficient alkenes: Bäckvall, J.-E.; Juntunen, S. K. J. Am. Chem. Soc. 1987, 109, 6393.
30. Croce, P. D.; La Rosa, C.; Zecchi, G. J. Chem. Soc., Perkin Trans. 1 1985, 2621.
31. For a general review of 1,3-dipolar cycloadditions, see: 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: New York, 1984; Vols. 1 and 2.
32. See ref 9a, Chapter 6.
33. Rauk, A. Orbital Interaction Theory of Organic Chemistry; Wiley: New York, 1994; pp 194-197.
34. For 1,3-dipolar cycloadditions of azides, see: (a) Sheradsky, T. In The Chemistry of the Azido Group; Patai, S., Ed.; Wiley: London, 1971; Chapter 6. For other 1,3-dipolar cycloadditions of 14, see: (b) Tsuge, O.; Kanemasa, S.; Matsuda, K. Chem Lett. 1983, 1131.
35. For 1,3-dipolar cycloadditions of azides, see: (a) Sheradsky, T. In The Chemistry of the Azido Group; Patai, S., Ed.; Wiley: London, 1971; Chapter 6. For other 1,3-dipolar cycloadditions of 14, see: (b) Tsuge, O.; Kanemasa, S.; Matsuda, K. Chem Lett. 1983, 1131.
36. For 1,3-dipolar cycloadditions of diazo compounds, see: Wulfman, D. S.; Linstrumelle, G.; Cooper, C. F. In The Chemistry of Diazonium and Diazo Groups; Patai, S., Ed.; Wiley: Chichester, 1978; Part 2, Chapter 18.
37. For 1,3-dipolar cycloadditions of nitrile oxides, see: Torsell, K. B. G. Nitrile Oxides, Nitrones and Nitronates in Organic Synthesis; VCH: Weinheim, 1988.
38. Snider, B. B.; Kirk, T. C.; Roush, D. M.; Gonzalez, D. J. Org. Chem. 1980, 45, 5015.
39. Numerous β-(phenylseleno)vinyl sulfones of regiochemistry opposite that of product 24 [i.e., R(PhSe)C=CHTs] have been prepared by the selenosulfonation of terminal acetylenes. The olefinic protons of these compounds have NMR signals at significantly higher field (ca. δ 6 ppm) than 24 (δ 7.20 ppm), thereby supporting the structure assignment of the latter product. See: Back, T. G.; Collins, S.; Kerr, R. G. J. Org. Chem. 1983, 48, 3077.
40. Back, T. G.; Birss, V. I.; Edwards, M.; Krishna, M. V. J. Org. Chem. 1988, 53, 3815.
41. See: (a) Reference 9a, Chapter 7. (b) Tidwell, T. T. Ketenes; Wiley: New York, 1995; Chapter 5. (c) Brady, W. T. In The Chemistry of Ketenes, Allenes and Related Compounds; Patai, S., Ed.; Wiley: Chichester, 1980; Part 1, Chapter 8.
42. See: (a) Reference 9a, Chapter 7. (b) Tidwell, T. T. Ketenes; Wiley: New York, 1995; Chapter 5. (c) Brady, W. T. In The Chemistry of Ketenes, Allenes and Related Compounds; Patai, S., Ed.; Wiley: Chichester, 1980; Part 1, Chapter 8.
43. See: (a) Reference 9a, Chapter 7. (b) Tidwell, T. T. Ketenes; Wiley: New York, 1995; Chapter 5. (c) Brady, W. T. In The Chemistry of Ketenes, Allenes and Related Compounds; Patai, S., Ed.; Wiley: Chichester, 1980; Part 1, Chapter 8.
44. For a review of ketene equivalents, see: Ranganathan, S.; Ranganathan, D.; Mehrotra, A. K. Synthesis 1977, 289.
45. For some previous examples of synthetic equivalents of ketene, see: (a) Corey, E. J.; Ravindranathan, T.; Terashima, S. J. Am. Chem. Soc. 1971, 93, 4326. (b) Trost, B. M.; Tamaru, Y. J. Am. Chem. Soc. 1975, 97, 3528. (c) Evans, D. A.; Scott, W. L.; Truesdale, L. K. Tetrahedron Lett. 1972, 121. (d) Bartlett, P. A.; Green, F. R., III; Webb, T. R. Tetrahedron Lett. 1977, 331.
46. For some previous examples of synthetic equivalents of ketene, see: (a) Corey, E. J.; Ravindranathan, T.; Terashima, S. J. Am. Chem. Soc. 1971, 93, 4326. (b) Trost, B. M.; Tamaru, Y. J. Am. Chem. Soc. 1975, 97, 3528. (c) Evans, D. A.; Scott, W. L.; Truesdale, L. K. Tetrahedron Lett. 1972, 121. (d) Bartlett, P. A.; Green, F. R., III; Webb, T. R. Tetrahedron Lett. 1977, 331.
47. For some previous examples of synthetic equivalents of ketene, see: (a) Corey, E. J.; Ravindranathan, T.; Terashima, S. J. Am. Chem. Soc. 1971, 93, 4326. (b) Trost, B. M.; Tamaru, Y. J. Am. Chem. Soc. 1975, 97, 3528. (c) Evans, D. A.; Scott, W. L.; Truesdale, L. K. Tetrahedron Lett. 1972, 121. (d) Bartlett, P. A.; Green, F. R., III; Webb, T. R. Tetrahedron Lett. 1977, 331.
48. For some previous examples of synthetic equivalents of ketene, see: (a) Corey, E. J.; Ravindranathan, T.; Terashima, S. J. Am. Chem. Soc. 1971, 93, 4326. (b) Trost, B. M.; Tamaru, Y. J. Am. Chem. Soc. 1975, 97, 3528. (c) Evans, D. A.; Scott, W. L.; Truesdale, L. K. Tetrahedron Lett. 1972, 121. (d) Bartlett, P. A.; Green, F. R., III; Webb, T. R. Tetrahedron Lett. 1977, 331.
49. Back, T. G.; Collins, S.; Krishna, M. V.; Law, K.-W. J. Org. Chem. 1987, 52, 4258.
50. Dolby, L. J.; Marshall, K. S. Org. Prep. Proced. Int. 1969, 1, 229.
51. Nishiyama, K.; Tanaka, N. J. Chem. Soc., Chem. Commun. 1983, 1322.
52. Grundmann, C.; Richter, R. J. Org. Chem. 1968, 33, 476.
53. The large coupling constant of ca. J = 7 Hz is assigned to the 5-bond coupling of the methylene protons at the 3-position with those at the 6-position. Similar large couplings have been reported for other 1,4-cyclohexadienes: Durham, L. J.; Studebaker, J.; Perkins, M. J. J. Chem. Soc., Chem. Commun. 1965, 456.
54. 1H NMR (200 MHz) δ 8.08 (d, J = 8.4 Hz), 6.71 (s), 2.49 (s), 2.26 (s), 1.72 (s).
55. (a) Trost, B. M.; Verhoeven, T. R. J. Am. Chem. Soc. 1980, 102, 4743.
56. (b) Trost, B. M.; Arndt, H. C.; Strege, P. E.; Verhoeven, T. R. Tetrahedron Lett. 1976, 3477.
57. Dictionary of Organic Compounds, 6th ed.; Cadogan, J. I. G., Ley, S. V., Pattenden, G., Raphael, R. A., Rees, C. W., Eds.; Chapman and Hall: London, 1996; Vol. 3, entry D-0-09403. The mp of the o-tolyl p-tolyl sulfone isomer of 33 is 60°C and therefore considerably lower; see entry D-0-0941.