Tetrahedron letters

1, 3-Dioxolan-2-ylium cations from acylfurans: Conversion of furyl ketones to esters under nonoxidative conditions

JA Bender, S Daves, FG West

Index: Bender, John A.; Daves, Samantha; West Tetrahedron Letters, 1998 , vol. 39, # 15 p. 2051 - 2054

Full Text: HTML

Citation Number: 4

Abstract

Acylfurans 3 furnished tosylated glycol monoesters 5 when treated with 1, 2-diols in the presence of an equivalent of TsOH. This process likely occurs via protiodefuranation of the intermediate furyl ketals to form 1, 3-dioxolan-2-ylium cations 8. Subsequent ring-opening via SN2 nucleophilic displacement by p-toluenesulfonate then provides esters 5. When a 1, 3-diol was employed, furan-containing ester 9 was formed instead of the standard product ...

Related Articles:

Reaction of singlet oxygen with azines: Implications for dioxirane intermediate

[Tetrahedron Letters, , vol. 25, # 8 p. 853 - 856]

Oxidation using quaternary ammonium polyhalides. III. An effective oxidation of alcohols and ethers by the use of benzyltrimethylammonium tribromide.

[Bulletin of the Chemical Society of Japan, , vol. 62, # 8 p. 2585 - 2588]

Ruthenium colloids: A new catalyst for alkane oxidation by tBHP in a biphasic water-organic phase system

[Tetrahedron Letters, , vol. 39, # 11 p. 1353 - 1356]

Direct Oxidation of Methyl Ethers to Carbonyl Compounds with a Combination of Nitrogen Dioxide and Water in the Presence or Absence of Ozone.

[Bulletin of the Chemical Society of Japan, , vol. 70, # 12 p. 3111 - 3115]

Catalytic Beckmann rearrangement of ketoximes in ionic liquids

[Tetrahedron Letters, , vol. 42, # 3 p. 403 - 405]

More Articles...