Oxidative seco rearrangement. A novel carbon-carbon bond cleavage

BM Trost, K Hiroi, LN Jungheim

Index: Trost, Barry M.; Hiroi, Kunio; Jungheim, Louis N. Journal of Organic Chemistry, 1980 , vol. 45, # 10 p. 1839 - 1847

Full Text: HTML

Citation Number: 24

Abstract

Trost, Hiroi, and Jungheim compounds with lead tetraacetate under many different conditions led to no detectable ring cleavage. We were able to isolate 2-acetoxy-2- (methylthio)-(or (phenylthio)) cyclohexanone. Reasoning that the initial attack occurred at sulfur to give 2 but that CC bond cleavage was too slow relative to sulfur serving as a leaving group to give 3 and 4, we felt we might achieve ring cleavage if the ionization of ...

Related Articles:

Weinreb amide based building blocks for convenient access to 1, 1-diarylethenes and isocombretastatin analogues

[Balasubramaniam, Sivaraman; Kommidi, Harikrishna; Aidhen, Indrapal Singh Tetrahedron Letters, 2011 , vol. 52, # 21 p. 2683 - 2686]

A new synthesis of 2-substituted-1, 3-dithianes from trichloromethyl compounds

[Rivera, Nancy Gonzalez; Becerril, David Corona; Guadarrama-Perez, Carlos; Covarrubias-Zuniga, Adrian; Avila-Zarraga, Jose Gustavo; Romero-Ortega, Moises Tetrahedron Letters, 2007 , vol. 48, # 7 p. 1201 - 1204]

Convenient ketone synthesis via N-acylaziridines

[Wattanasin, S.; Kathawala, F.G. Tetrahedron Letters, 1984 , vol. 25, # 8 p. 811 - 814]

Lewis acid mediated addition of 2-acyl-1, 3-dithianes to α, β-unsaturated ketones: Synthesis of cyclohexenedione mono-dithioacetals.

[Bulman Page, Philip C.; Marchington, Allan P.; Graham, Lisa J.; Harkin, Shaun A.; Wood, William W. Tetrahedron, 1993 , vol. 49, # 45 p. 10369 - 10386]

Direct ni mediated synthesis of ketones from acyl bromides and grignard reagents

[Malanga, Corrado; Aronica, Laura A.; Lardicci, Luciano Tetrahedron Letters, 1995 , vol. 36, # 50 p. 9185 - 9188]

More Articles...