Synthesis of Alkenes with Pyramidalized Double Bonds - Unnatural Products of Theoretical Interest

Synlett

Volumn 1996, Issue 8, 1996, Pages 711-719

  Borden, Weston Thatcher ^a  

^a UNIVERSITY OF WASHINGTON   (United States)

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EID: 0000511244     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5504     Document Type: Article

References (96)

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48. 2 from the 31.6 kcal/mol that we calculated at the SDCI level with a DZ basis set to 11.3 kcal/mol at the QCISD(T)/6-31G**//MP2/6-31G** level; Sauers, R. R. Tetrahedron Lett. 1994, 7213. The transition state for cleavage of one C-O bond was not located in the latter study; so it is currently unknown whether calculations, performed at correlated levels of theory with a polarized basis set, will still find one-bond cleavage to be the lower energy reaction pathway.
49. 2 from the 31.6 kcal/mol that we calculated at the SDCI level with a DZ basis set to 11.3 kcal/mol at the QCISD(T)/6-31G**//MP2/6-31G** level; Sauers, R. R. Tetrahedron Lett. 1994, 7213. The transition state for cleavage of one C-O bond was not located in the latter study; so it is currently unknown whether calculations, performed at correlated levels of theory with a polarized basis set, will still find one-bond cleavage to be the lower energy reaction pathway.
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53. Similar reactions have subsequently been used to prepare unstrained alkenes from diols; Hanessian, S.; Bargiotti, A.; LaRue, M. Tetrahedron Lett. 1978, 737; King, J. L.; Posner, B. A.; Mak, K. T.; Yang, N. C. Tetrahedron Lett. 1987, 3919.
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56. 15 Substituting benzene for cyclohexane as the solvent suppressed formation of the latter product.
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65. 52 In the case of the homologous series 8, the reference alkene is bicyclo[3.3.0]oct-1(5)-ene (8, n = ∞).
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79. Wyvratt, M. J.; Paquette, L. A. J. Am. Chem. Soc. 1974, 96, 4671; McNeil, D.; Vogt, B. R.; Sudol, S.; Theodoropoulos, S.; Hedaya, E. J. Am. Chem. Soc. 1974, 96, 4673; Taylor, R. T.; Pelter, M. W.; Paquette, L. A. Org. Syn. 1989, 68, 198.
80. Wyvratt, M. J.; Paquette, L. A. J. Am. Chem. Soc. 1974, 96, 4671; McNeil, D.; Vogt, B. R.; Sudol, S.; Theodoropoulos, S.; Hedaya, E. J. Am. Chem. Soc. 1974, 96, 4673; Taylor, R. T.; Pelter, M. W.; Paquette, L. A. Org. Syn. 1989, 68, 198.
81. Wyvratt, M. J.; Paquette, L. A. J. Am. Chem. Soc. 1974, 96, 4671; McNeil, D.; Vogt, B. R.; Sudol, S.; Theodoropoulos, S.; Hedaya, E. J. Am. Chem. Soc. 1974, 96, 4673; Taylor, R. T.; Pelter, M. W.; Paquette, L. A. Org. Syn. 1989, 68, 198.
82. Mishler, B. J.; Borden, W. T., unpublished results.
83. Diacid 48 is prepared from the diester formed by transannular oxidative ring closure of the dianion of 1,5-dimethyl-3,7-dicarbomethoxybicyclo[3.3.0]octane; Camps, P.; Iglesias, C.; Rodriguez, M. J.; Grancha, M. D.; Oregon, M. E.; Lozano, R.; Miranda, M. A.; Figuerdo, M.; Linares, A. Chem. Ber. 1988, 121, 647.
84. (a) Johnson, W. T.; Borden, W. T., unpublished results.
85. (b) The alkene has also been trapped as Diels-Alder adducts; and, upon heating, the dimer (51) undergoes cyclobutane ring opening to a diene; Camps, P.; Font-Bardi, M.; Pérez, F.; Solans, X.; Vázquez, S. Angew. Chem. Int. Ed. Engl. 1995, 34, 912.
86. Wood, G.; Woo, E. P. Can. J. Chem. 1968, 46, 3173.
87. (a) Greenhouse, R.; Ravindranathan, T.; Borden, W. T. J. Am. Chem. Soc., 1976, 98, 6738;
88. (b) Greenhouse, R.; Ravindranathan, T.; Borden, W. T.; Hirotsu, K.; Clardy, J. J. Am. Chem. Soc. 1977, 99, 6955.
89. Review: Warner, P. M. Chem. Rev. 1989, 89, 1067.
90. Hrovat, D. A.; Miyake, F.; Trammell, G.; Gilbert, K. E.; Mitchell, J.; Clardy, J.; Borden, W. T. J. Am. Chem. Soc., 1987, 109, 5524.
91. Smith, J. M., Ph.D. thesis, University of Washington, 1993.
92. 2 to form an epoxide has been found in a torsionally strained alkene; Lease, T. G.; Shea, K. E. J. Am. Chem. Soc. 1993, 115, 2248.
93. For a discussion of and leading references to interactions between cations and π bonds see Kearney, P. C.; Mizoue, L. S.; Kumpf, R. A.; Forman, J. E.; McCurdy, A.; Dougherty, D. A. J. Am. Chem. Soc. 1993, 115, 9907.
94. Smith, J. M.; Hrovat, D. A.; Borden, W. T.; Allan, M.; Asmis, K. R.; Bulliard, C.; Haselbach, E.; Meier, U. C. J. Am. Chem. Soc. 1993, 115, 3816.
95. More recently, the stability of 8, n = 3, has allowed us to attempt to measure its gas-phase proton affinity (PA), relative to that of 8, n = "∞". The results of ab initio calculations indicate that the unexpectedly high PA observed results from formation of the cyclopropylcarbinyl cation that would be generated by protonation of vinylcyclopropane 35, n = 3. Cleven, C. D.; Hoke, S. H.; Cooks, R. G.; Hrovat, D. A.; Borden, W. T., submitted.
96. Nicolaides, A.; Smith, J. M.; Kumar, A.; Barnhart, D.; Borden, W. T. Organometallics 1995, 14, 3475.