Tetrahedron

Synthesis and chemical diversity analysis of bicyclo [3.3. 1] non-3-en-2-ones

…, J Contreras-García, AM Virshup, DN Beratan, W Yang…

Index: Hammill, Jared T.; Contreras-Garcia, Julia; Virshup, Aaron M.; Beratan, David N.; Yang, Weitao; Wipf, Peter Tetrahedron, 2010 , vol. 66, # 31 p. 5852 - 5862

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Citation Number: 4

Abstract

Functionalized bicyclo [3.3. 1] non-3-en-2-ones are obtained from commercially available phenols by a hypervalent iodine oxidation, enone epoxidation, epoxide thiolysis, and intramolecular aldol reaction sequence. Reaction optimization studies identified room temperature as well as microwave-mediated procedures, providing moderate to good yields (57–88%) in the thiophenol-mediated epoxide opening and intramolecular aldol reaction. ...

~96%

~86%

~85%

Oxidation of hydroquinone silyl ethers to quinones

[Stewart, Ray F.; Miller, Larry L. Journal of the American Chemical Society, 1980 , vol. 102, # 15 p. 4999 - 5004]

Mixed methyl-silyl ketals of quinones. Their preparation via...

[Stern, Alan; Swenton, John S. Journal of Organic Chemistry, 1987 , vol. 52, # 13 p. 2763 - 2768]

Phenolic oxidation with (diacetoxyiodo) benzene

[Pelter, Andrew; Elgendy, Said Tetrahedron Letters, 1988 , vol. 29, # 6 p. 677 - 680]

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[Coutts, Ian G. C.; Culbert, Nicholas J.; Edwards, Mark; Hadfield, John A.; Musto, Donald R.; et al. Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1985 , p. 1829 - 1836]