Synthesis and cycloaddition reactions of 1-(arylthio)-1,3-dienes. A combined experimental and theoretical study of bicyclic adducts structures

Journal of Organic Chemistry

Volumn 61, Issue 16, 1996, Pages 5290-5306

  Maddaluno, Jacques ^a   Gaonac'h, Odile ^a   Marcual, Albert ^a   Toupet, Loïc ^b   Giessner Prettre, Claude ^c  

^a UNIVERSITÉ DE ROUEN   (France)

^b UNIVERSITÉ DE RENNES 1   (France)

^c CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000449365     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9519120     Document Type: Article

References (99)

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47. Stereochemistry of diene 7b is not thermally altered, as checked by warming it alone.
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49. See for instance: (a) Danishefsky, S.; Yan, C. F.; Mc Curry, P. M. J. Org. Chem. 1977, 42, 1819. (b) Overman, L. E.; Petty, C. B.; Ban, T.; Huang, G. T. J. Am. Chem. Soc. 1983, 105, 6335. (c) Blatcher, P.; Warren, S. J. Chem. Soc., Perkin Trans. 1 1985, 1055. (d) Tripathy, R.; Franck, R. W.; Onan, K. D. J. Am. Chem. Soc. 1988, 110, 3257. (e) Branchadell, V.; Sodupe, M.; Ortuno, R. M.; Oliva, A.; Gomez-Pardo, A.; Guingant, A.; D'Angelo, J. J. Org. Chem. 1991, 56, 4135.
50. See for instance: (a) Danishefsky, S.; Yan, C. F.; Mc Curry, P. M. J. Org. Chem. 1977, 42, 1819. (b) Overman, L. E.; Petty, C. B.; Ban, T.; Huang, G. T. J. Am. Chem. Soc. 1983, 105, 6335. (c) Blatcher, P.; Warren, S. J. Chem. Soc., Perkin Trans. 1 1985, 1055. (d) Tripathy, R.; Franck, R. W.; Onan, K. D. J. Am. Chem. Soc. 1988, 110, 3257. (e) Branchadell, V.; Sodupe, M.; Ortuno, R. M.; Oliva, A.; Gomez-Pardo, A.; Guingant, A.; D'Angelo, J. J. Org. Chem. 1991, 56, 4135.
51. See for instance: (a) Danishefsky, S.; Yan, C. F.; Mc Curry, P. M. J. Org. Chem. 1977, 42, 1819. (b) Overman, L. E.; Petty, C. B.; Ban, T.; Huang, G. T. J. Am. Chem. Soc. 1983, 105, 6335. (c) Blatcher, P.; Warren, S. J. Chem. Soc., Perkin Trans. 1 1985, 1055. (d) Tripathy, R.; Franck, R. W.; Onan, K. D. J. Am. Chem. Soc. 1988, 110, 3257. (e) Branchadell, V.; Sodupe, M.; Ortuno, R. M.; Oliva, A.; Gomez-Pardo, A.; Guingant, A.; D'Angelo, J. J. Org. Chem. 1991, 56, 4135.
52. See for instance: (a) Danishefsky, S.; Yan, C. F.; Mc Curry, P. M. J. Org. Chem. 1977, 42, 1819. (b) Overman, L. E.; Petty, C. B.; Ban, T.; Huang, G. T. J. Am. Chem. Soc. 1983, 105, 6335. (c) Blatcher, P.; Warren, S. J. Chem. Soc., Perkin Trans. 1 1985, 1055. (d) Tripathy, R.; Franck, R. W.; Onan, K. D. J. Am. Chem. Soc. 1988, 110, 3257. (e) Branchadell, V.; Sodupe, M.; Ortuno, R. M.; Oliva, A.; Gomez-Pardo, A.; Guingant, A.; D'Angelo, J. J. Org. Chem. 1991, 56, 4135.
53. 1H NMR spectroscopy; selectivities have not been determined.
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55. Adduct 29 is also obtained as a single (endo) isomer.
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61. The unusually large amount of aromatic material 37 recovered could however be due to an easy double 1,2-diaxial anti elimination made possible by a convex structure of the following type: (Equation Presented)
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70. Warming up 25 to reflux of xylenes only leads to a slow degradation/aromatization of this structure.
71. This problem is still at the heart of active debates: (a) Rivera-Gaines, V. E.; Leibowitz, S. J.; Laane, J. J. Am. Chem. Soc. 1991, 113, 9735. (b) Anet, F. A. L.; Freedberg, D. I.; Storer, J. W.; Houk, K. N. J. Am. Chem. Soc. 1992, 114, 10969. (c) Anet, F. A. L. In The Conformational Analysis of Cyclohexenes, Cyclohexadienes, and Related Hydroaromatic Compounds; Rabideau, P. W., Ed.; VCH: New York, 1989. (d) Laane, J.; Choo, J. J. Am. Chem. Soc. 1994, 116, 3889. (e) Sieburth S. Mc. N. J. Chem. Soc., Chem. Commun. 1994, 1663.
72. This problem is still at the heart of active debates: (a) Rivera-Gaines, V. E.; Leibowitz, S. J.; Laane, J. J. Am. Chem. Soc. 1991, 113, 9735. (b) Anet, F. A. L.; Freedberg, D. I.; Storer, J. W.; Houk, K. N. J. Am. Chem. Soc. 1992, 114, 10969. (c) Anet, F. A. L. In The Conformational Analysis of Cyclohexenes, Cyclohexadienes, and Related Hydroaromatic Compounds; Rabideau, P. W., Ed.; VCH: New York, 1989. (d) Laane, J.; Choo, J. J. Am. Chem. Soc. 1994, 116, 3889. (e) Sieburth S. Mc. N. J. Chem. Soc., Chem. Commun. 1994, 1663.
73. This problem is still at the heart of active debates: (a) Rivera-Gaines, V. E.; Leibowitz, S. J.; Laane, J. J. Am. Chem. Soc. 1991, 113, 9735. (b) Anet, F. A. L.; Freedberg, D. I.; Storer, J. W.; Houk, K. N. J. Am. Chem. Soc. 1992, 114, 10969. (c) Anet, F. A. L. In The Conformational Analysis of Cyclohexenes, Cyclohexadienes, and Related Hydroaromatic Compounds; Rabideau, P. W., Ed.; VCH: New York, 1989. (d) Laane, J.; Choo, J. J. Am. Chem. Soc. 1994, 116, 3889. (e) Sieburth S. Mc. N. J. Chem. Soc., Chem. Commun. 1994, 1663.
74. This problem is still at the heart of active debates: (a) Rivera-Gaines, V. E.; Leibowitz, S. J.; Laane, J. J. Am. Chem. Soc. 1991, 113, 9735. (b) Anet, F. A. L.; Freedberg, D. I.; Storer, J. W.; Houk, K. N. J. Am. Chem. Soc. 1992, 114, 10969. (c) Anet, F. A. L. In The Conformational Analysis of Cyclohexenes, Cyclohexadienes, and Related Hydroaromatic Compounds; Rabideau, P. W., Ed.; VCH: New York, 1989. (d) Laane, J.; Choo, J. J. Am. Chem. Soc. 1994, 116, 3889. (e) Sieburth S. Mc. N. J. Chem. Soc., Chem. Commun. 1994, 1663.
75. This problem is still at the heart of active debates: (a) Rivera-Gaines, V. E.; Leibowitz, S. J.; Laane, J. J. Am. Chem. Soc. 1991, 113, 9735. (b) Anet, F. A. L.; Freedberg, D. I.; Storer, J. W.; Houk, K. N. J. Am. Chem. Soc. 1992, 114, 10969. (c) Anet, F. A. L. In The Conformational Analysis of Cyclohexenes, Cyclohexadienes, and Related Hydroaromatic Compounds; Rabideau, P. W., Ed.; VCH: New York, 1989. (d) Laane, J.; Choo, J. J. Am. Chem. Soc. 1994, 116, 3889. (e) Sieburth S. Mc. N. J. Chem. Soc., Chem. Commun. 1994, 1663.
76. See ref 37d for a comparable observation.
77. 43
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85. In agreement with a personal suggestion by Dr. S. Warren but in contradiction with Kwart, H.; Johnson, N. J. Am. Chem. Soc. 1970, 92, 6064 and ref 44c. See also in relation recent evidences about photochemical [1,3]-stannyl migration of 3-aryl-substituted allyltins: Takuwa, A.; Kanaue, T.; Nishigaichi, Y.; Iwamoto, H. Tetrahedron Lett. 1995, 36, 575.
86. In agreement with a personal suggestion by Dr. S. Warren but in contradiction with Kwart, H.; Johnson, N. J. Am. Chem. Soc. 1970, 92, 6064 and ref 44c. See also in relation recent evidences about photochemical [1,3]-stannyl migration of 3-aryl-substituted allyltins: Takuwa, A.; Kanaue, T.; Nishigaichi, Y.; Iwamoto, H. Tetrahedron Lett. 1995, 36, 575.
87. See for instance: (a) Liu, P.; Whitham, G. H. J. Chem. Soc., Chem. Commun. 1983, 1102. (b) Padwa, A.; Bullock, W. H.; Dyszlewski, A. D. Tetrahedron Lett. 1987, 28, 3193; J. Org. Chem. 1990, 55, 955. (c) Jones-Hertzog, D. K.; Jorgensen, W. L. J. Am. Chem. Soc. 1995, 117, 9077.
88. See for instance: (a) Liu, P.; Whitham, G. H. J. Chem. Soc., Chem. Commun. 1983, 1102. (b) Padwa, A.; Bullock, W. H.; Dyszlewski, A. D. Tetrahedron Lett. 1987, 28, 3193; J. Org. Chem. 1990, 55, 955. (c) Jones-Hertzog, D. K.; Jorgensen, W. L. J. Am. Chem. Soc. 1995, 117, 9077.
89. See for instance: (a) Liu, P.; Whitham, G. H. J. Chem. Soc., Chem. Commun. 1983, 1102. (b) Padwa, A.; Bullock, W. H.; Dyszlewski, A. D. Tetrahedron Lett. 1987, 28, 3193; J. Org. Chem. 1990, 55, 955. (c) Jones-Hertzog, D. K.; Jorgensen, W. L. J. Am. Chem. Soc. 1995, 117, 9077.
90. See for instance: (a) Liu, P.; Whitham, G. H. J. Chem. Soc., Chem. Commun. 1983, 1102. (b) Padwa, A.; Bullock, W. H.; Dyszlewski, A. D. Tetrahedron Lett. 1987, 28, 3193; J. Org. Chem. 1990, 55, 955. (c) Jones-Hertzog, D. K.; Jorgensen, W. L. J. Am. Chem. Soc. 1995, 117, 9077.
91. Gilchrist, T. L.; Storr, R. C. Organic Reactions and Orbital Symmetry; Cambridge University Press: London, 1972; p 240.
92. (a) Fair, C. K. MolEN: an Interactive Intelligent System for Crystal Structure Analysis; Enraf-Nonius: Delft, The Netherlands, 1990.
93. (b) International Tables for X-Ray Crystallography, Vol. IV; Kynoch Press: Birmingham, U.K., 1974.
94. (c) Johnson, C. K. ORTEP, Report ORNL-3794, Oakridge National Laboratory, Tennessee, 1965.
95. Obtained by averaging eqs 5 and 8 in Haasnoot, C. A. G.; De Leeuw, F. A. A. M.; Altona, C. Tetrahedron 1980, 36, 2783. The electronegativities of substituants have been neglected for eq 8 since the strain induced by bicyclic structures could not be taken into account while probably of prime importance in this system. The equation retained here gives fair account for threshold values.
96. (a) Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. P. J. J. Am. Chem. Soc. 1985, 107, 3902.
97. (b) Dewar, M. J. S.; Yuan, Y. C. Inorg. Chem. 1990, 29, 3881.
98. GAUSSIAN 92, Revision B: Frisch, M. B.; Trucks, G. W.; Head-Gordon, M.; Gill, P. M. W.; Wong, M. W.; Foresman, J. B.; Johnson, B. G.; Schlegel, H. B.; Robb, M.A.; Replogle, E. S.; Gonperts, R.; Andres, J. L.; Raghavachari, K.; Binkley, J. S.; Gonzalez, C.; Martin, R. L.; Fox, D. J.; Defrees, D. J.; Baker, J.; Stewart, J.J. P.; Pople, J. A., Gaussian, Inc., Pittsburgh, PA, 1992.
99. The authors have deposited atomic coordinates for structures 25 and 28 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.