Evaluation of 1, 3-diaxial steric hindrance to proton abstraction alpha to carbonyl groups
…, JM Dostal, JD Trometer, TA Spencer
Index: Gula, M. J.; Vitale, D. E.; Dostal, J. M.; Trometer, J. D.; Spencer, T. A. Journal of the American Chemical Society, 1988 , vol. 110, # 13 p. 4400 - 4405
Full Text: HTML
Citation Number: 10
Abstract
Abstract: An assessment of the magnitude of steric hindrance by axial substituents to abstraction of syn-axial protons alpha to carbonyl groups in trans-fused decalones has been made by a comparison of the rates of reactions of beta acetoxy ketones 7, 4, 8, and 9 to form enones 18, 5, 26, and 27, respectively, in the presence of four bases (hydroxide ion, morpholine, N-methylmorpholine, and N-ethylmorpholine). For all the reactions of 7 and 4, ...
Related Articles:
[Wada, Eiji; Funakoshi, Junji; Kanemasa, Shuji Bulletin of the Chemical Society of Japan, 1992 , vol. 65, # 9 p. 2456 - 2464]
[Combs-Walker, Lucille A.; Hill, Craig L. Journal of the American Chemical Society, 1992 , vol. 114, # 3 p. 938 - 946]
Arylation of 8??Acetoxyoctalenone in a Nickel??Catalyzed Coupling Reaction with Lithium Arylborates
[Kobayashi, Yuichi; Ito, Michiko European Journal of Organic Chemistry, 2000 , # 20 p. 3393 - 3397]
[Bestmann, Hans Juergen; Schade, Gerold; Luetke, Harry; Moenius, Thomas Chemische Berichte, 1985 , vol. 118, # 7 p. 2640 - 2658]
[Sato, Tsuneo; Wakahara, Yoshiyuki; Otera, Junzo; Nozaki, Hitosi Tetrahedron Letters, 1990 , vol. 31, # 11 p. 1581 - 1584]