Electrophile-initiated selective ring transformations of cyclopropyl ketones
M Demuth, G Mikhail
Index: Demuth, Martin; Mikhail, Gamal Tetrahedron, 1983 , vol. 39, # 6 p. 991 - 997
Full Text: HTML
Citation Number: 28
Abstract
Electrophile-mediated cyclopropane cleavage in tricyclo [3.3. 0.02, 8] octan-3-one (1a) is increasingly directed towards the maximum bond overlap site in the following order of reagents: acetyl methanesulfonate,+ Br-or I-; t-butyl-dimethylsilyl iodide; t-butyldimethylsilyl trifluoroacetate; trimethylsilyl trifluoroacetate. The latter reagent gives rise to one single regioisomer (→ 6a). Routine yields of isolated products lie between 78 and 87%. ...
Related Articles:
Rhenium-catalyzed reaction of carbonyl compounds with ketene silyl acetals
[Nishiyama, Yutaka; Kaiba, Kenta; Umeda, Rui Tetrahedron Letters, 2010 , vol. 51, # 5 p. 793 - 795]
Thiazolium-catalyzed additions of acylsilanes: a general strategy for acyl anion addition reactions
[Veysoglu, Tarik; Mitscher, Lester A. Tetrahedron Letters, 1981 , vol. 22, # 14 p. 1299 - 1302]
Thiazolium-catalyzed additions of acylsilanes: a general strategy for acyl anion addition reactions
[Veysoglu, Tarik; Mitscher, Lester A. Tetrahedron Letters, 1981 , vol. 22, # 14 p. 1299 - 1302]
Selectivity in the reactions of alkyllithium reagents with α, ω-dichloropermethylsiloxanes
[Kazoura, Samih Amine; Weber, Wolliam P. Journal of Organometallic Chemistry, 1983 , vol. 243, # 2 p. 149 - 156]
Supported gold nanoparticle catalyst for the selective oxidation of silanes to silanols in water
[Mitsudome, Takato; Noujima, Akifumi; Mizugaki, Tomoo; Jitsukawa, Koichiro; Kaneda, Kiyotomi Chemical Communications, 2009 , # 35 p. 5302 - 5304]