151158-69-9Relevant academic research and scientific papers
Synthesis and cycloaddition reactions of 1-(arylthio)-1,3-dienes. A combined experimental and theoretical study of bicyclic adducts structures
Maddaluno, Jacques,Gaonac'h, Odile,Marcual, Albert,Toupet, Loic,Giessner-Prettre, Claude
, p. 5290 - 5306 (2007/10/03)
A method giving simple access to various 1-(phenylthio)-4-substituted-1,3-dienes (5-10) is described. The influence of the different functionalizations introduced on the dienic systems has been tested in a set of classical [4 + 2] cycloaddition reactions. Both the endo/exo and regio selectivities have been investigated. While the endo compound is, as expected, the only or major isomer in all cases, the regio competition between sulfur and oxygen is in favor of the oxygen substituent in the case studied here, in contrast to related works. For one type of adduct, X-ray crystallographic analysis and NMR spectroscopy have been used in conjunction with ab initio and semiempirical AM1 calculations to determine the structure and conformations of products as well as the energetic pathway from the primary concave endo cycloadduct (28) to a rearranged bicyclic structure (39). The theoretical results fully support the occurrence of a photochemical [1,3] sigmatropic shift of the thiophenyl group.
Conjugate-Elimination on Unsaturated Acetals: A One-Step Route to Functionalized 1,3-Dienes
Maddaluno, Jacques,Gaonac'h, Odile,Gallic, Yann Le,Duhamel, Lucette
, p. 8591 - 8594 (2007/10/02)
γ-Functionalized α,β-unsaturated dimethyl acetals undergo a methanol δ-elimination upon basic treatment, leading to 1,4-disubstituted 1,3-dienes in good yields and, in several cases, with high stereocontrol of the newly formed double bonds.
A MILD AND DIRECT OXIDATION OF DIENOL THIOETHERS INTO KETENE DITHIOACETALS.
Freidanck, Frank,Maddaluno, Jacques F.,Gaonac'h, Odile,Duhamel, Lucette
, p. 3871 - 3874 (2007/10/02)
Functionalized dienol thioethers reacts with 3 eq. of thiophenol at room temperature in presence of dioxygen to give directly corresponding ketene dithioacetals in high yields.
