Origin of the preference for the chair conformation in the Cope rearrangement. Effect of phenyl substituents on the chair and boat transition states
…, GJ Stoddard, WP England, CD Haffner
Index: Shea; Stoddard; England; Haffner Journal of the American Chemical Society, 1992 , vol. 114, # 7 p. 2635 - 2643
Full Text: HTML
Citation Number: 17
Abstract
Abstract: d, l-and meso-2, 2'-bis [l-methylene-l, 2, 3, 4-tetrahydronaphthalenes] 8 and 9 were synthesized, and the activation energy parameters for their unimolecular [3, 3] sigmatropic rearrangement to 1, 2-bis (3, 4-dihydro-l-naphthalenyl) ethane (13) were determined. The d, l diastereomer is constrained to undergo Cope rearrangement in the chair conformation while the meso diastereomer is constrained to the boat. At 150 OC kd,,/k,,= 7 X IO6. A ...
Related Articles:
[Chacon-Garcia, Luis; Martinez, Roberto European Journal of Medicinal Chemistry, 2002 , vol. 37, # 3 p. 261 - 266]
Oxidative Carbon− Carbon Bond Formation via Allyldimethylsilyl Enol Ethers
[Konkol, Leah C.; Jones, Brian T.; Thomson, Regan J. Organic Letters, 2009 , vol. 11, # 23 p. 5550 - 5553]
The case favoring direct C-alkylation of heteroatom-substituted enolates
[Solomon, Mark; Hoekstra, William; Zima, George; Liotta, Dennis Journal of Organic Chemistry, 1988 , vol. 53, # 21 p. 5058 - 5062]
Low-valent zirconocene-mediated cyclization of γ, δ-unsaturated oximes
[Kitamura, Mitsuru; Shintaku, Yuki; Kudo, Daisuke; Okauchi, Tatsuo Tetrahedron Letters, 2010 , vol. 51, # 37 p. 4890 - 4893]
The case favoring direct C-alkylation of heteroatom-substituted enolates
[Solomon, Mark; Hoekstra, William; Zima, George; Liotta, Dennis Journal of Organic Chemistry, 1988 , vol. 53, # 21 p. 5058 - 5062]