An Interesting Rearrangement of Unsaturated Sulphonate and Thiosulphonate Esters
Alkenyl tosylates and thiotosylates, in the presence of radical initiators, undergo radical rearrangements to the corresponding tetrahydrofuran and tetrahydrothiophen derivatives.
Copper-Catalyzed Oxysulfenylation of Enolates with Sodium Sulfinates: A Strategy to Construct Sulfenylated Cyclic Ethers
A new copper-catalyzed oxysulfenylation reaction of enolates with sodium sulfinates has been disclosed. A series of sulfenylated heterocycles including four- and seven-membered cyclic ether were obtained in mild to good yields. This reaction is proposed to go through a radical process, and the sulfur radical (RS?) may be a reactive species.
Preparation and synthetic applications of lithiated vinyl sulfones derived from 3-buten-1-ol and 4-penten-1-ol
Vinyl sulfones (E)-4-tosyl-3-bulen-1-ol (2) and its MOM-derivative 6, prepared by iodosulfonylation-dehydroiodination of 3-buten-1-ol(1), are regio and stereoselectively lithiated at die 4-position to afford intermediates 3 and 7, respectively. Tile prote
Caturla, Francisco,Najera, Carmen
p. 11449 - 11464
(2007/10/03)
The Cyclosulfonation Reaction: A Comment on the Radical Reactions of 4-Pentenyl Tosylate
Attempted free radical rearrangement of the para-toluenesulfonyl ester of 4-penten-1-ol in carbon tetrachloride gives only the simple Kharash 1,2-adduct, instead of the 2-substituted tetrahydrofuran as claimed by Serra and da Silva Correa.
Craig, Donald C.,Durie, Alexander,Edwards, Gavin L.,Sinclair, David J.
p. 1307 - 1310
(2007/10/02)
para-toluenesulfonyl iodide as a convenient, mild reagent for the preparation of functionalised cyclic ethers
Free radical addition of para-toluenesulfonyl iodide to alkenols occurs readily to give functionalised βiodosulfones as single regioisomers. Cyclisation to give cyclic ethers is effected by treatment with potassium carbonate in methanol. An anomalous reac
Edwards, Gavin L.,Walker, Katherine A.
p. 1779 - 1782
(2007/10/02)
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