Synthesis of Substituted 2,5-Dihydrothiophene-2-Carboxylic Acids by Lithium/Ammonia Reduction

Blenderman, Walter G.; Joullié, Madeleine M.

doi:10.1080/00397918108065742

Cited by 17 publications

(1 citation statement)

References 8 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Electrochemical reductions of acetylthiophene or benzoylthiophene also give pinacols . Reductions of alkanoylthiophenes with dissolving metals such as Li/NH 3 or Na/NH 3 give the corresponding 2,5-dihydro derivatives .…”

Section: Introductionmentioning

confidence: 99%

Coupling Reactions and Coupling−Alkylations of Thiophenecarbaldehydes Promoted by Samarium Diiodide

Yang

Fang

1998

J. Org. Chem.

View full text Add to dashboard Cite

The coupling reactions of 2-thiophenecarbaldehyde with aromatic or aliphatic aldehydes were promoted by samarium diiodide in the presence of hexamethylphosphoramide to give C-5 hydroxyalkylation products. The coupling reactions of 3-thiophenecarbaldehyde occurred at C-2, and the subsequent alkylations occurred at the sulfur atom, accompanied by a concurrent opening of the thiophene ring to afford γ-lactols. Double hydroxyalkylations of 2-and 3-thiophenecarbaldehydes were also carried out under appropriate reaction conditions. Synthetic applications of these thiophenecarbonyl coupling products were demonstrated, for example, by elaboration to furans, butenolides, and thiophene-fused polycyclic compounds.

show abstract

Section: Introductionmentioning

confidence: 99%

Coupling Reactions and Coupling−Alkylations of Thiophenecarbaldehydes Promoted by Samarium Diiodide

Yang

Fang

1998

J. Org. Chem.

View full text Add to dashboard Cite

show abstract

TheBirch Reduction of Aromatic Compounds

Rabideau

Marcinow²

1992

Organic Reactions

131

138

View full text Add to dashboard Cite

The reduction of aromatic compounds by alkali metals in liquid ammonia represents an important method for the preparation of partially unsaturated six‐membered rings. The reaction was discovered by Wooster and Godfrey, but the major development resulted from the efforts of A. J. Birch, and the reaction has since come to bear his name. Although a variety of metals can be used, the most common are sodium and lithium, and, to a lesser extent, potassium. Cosolvents such as ether or tetrahydrofuran (THF) are often used to improve solubility, and weak acids such as alcohols may be employed during the reaction as proton sources. The latter are necessary for the reduction of benzene and its unactivated derivatives. Improvement in experimental procedures by Wilds and Nelson, the application to polynuclear compounds by Hückel and later by Harvey, and the development of methods for the alkylation of the anions generated in this process (i.e., reductive alkylation) have made this reaction an important approach to the synthesis of a wide variety of organic compounds.

show abstract

Reduction and Desulfurization of Thiophene Compounds

Беленький

Gol'dfarb

1985

Chemistry of Heterocyclic Compounds: A Series of Monographs

View full text Add to dashboard Cite

Synthesis of Substituted 2,5-Dihydrothiophene-2-Carboxylic Acids by Lithium/Ammonia Reduction

Cited by 17 publications

References 8 publications

Coupling Reactions and Coupling−Alkylations of Thiophenecarbaldehydes Promoted by Samarium Diiodide

Coupling Reactions and Coupling−Alkylations of Thiophenecarbaldehydes Promoted by Samarium Diiodide

TheBirch Reduction of Aromatic Compounds

Reduction and Desulfurization of Thiophene Compounds

Contact Info

Product

Resources

About