2409-87-2Relevant academic research and scientific papers
Lithium/Ammonia Reductions of 2-Thiophenecarboxylic Acids
Blenderman, Walter G.,Joullie, Madeleine M.,Preti, George
, p. 3206 - 3213 (2007/10/02)
Lithium/ammonia reductions of 2-thiophenecarboxylic acids (1) in the absence of a proton source afforded mixtures of products.In the presence of methanol acyclic mercapto carboxylic acids (4) were the major products.Ring closure of 4 to the corresponding thiolactones (12) showed the double bonds in 4 to be of cis geometry.Attempts were made to prepare Z olefinic compounds derived from these mercapto carboxylic acids.Lithium 2-thiophenecarboxylate salts (2) afforded good yields of the corresponding 2,5-dihydro-2-thiophenecarboxylic acids (3).The presence of substituents on the ring and the ratio of metal to acid were significant factors in determining the nature of this products.A mechanism is proposed to explain the products observed.
STUDIES ON STRUCTURALLY SIMPLE α,β-BUTENOLIDES-I NEW SYNTHESIS OF RACEMIC γ-HYDROXYMETHYL-α,β-BUTENOLIDE AND DERIVATIVES
Cardellach, J.,Estopa, C.,Font, J.,Moreno-Manas, M.,Ortuno, R. M.,et al.
, p. 2377 - 2394 (2007/10/02)
Exhaustive approaches to the synthesis of racemic γ-heterosubstituted γ-methyl-α,β-butenolides are presented, starting from C3 synthons (glyceraldehyde, glycidaldehyde, acrolein and 2,3-epoxypropyl ethers).Good general methods for the preparation of γ-hydroxymethyl-α,β-butenolide 2, several of its ether derivatives, as well as of γ-bromomethyl-α,β-butenolide 5, are given.The reactivities of these structurally simple but highly functionalized compounds, convenient synthons for more complex molecules, are preliminarily explored.
