142434-95-5Relevant 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.
1-(Phenylthio)- and 1-(phenylsulfoxide)-4-alkoxy-butadienes, a new class of chiral dienes
Gaonac'h,Maddaluno,Ple,Duhamel
, p. 2473 - 2476 (2007/10/02)
Trans-acetalization of the methyl acetal of 3-methyl-4-(phenylthio)-but-2-enal 2a in acidic medium leads to the expected trans-acetals 2b-f or their γ-elimination products (i.e. 4-alkoxy-2-methyl-1-(phenylthio)buta-1,3-dienes 4), depending on the nature of the selected alcohol. Both types of compounds may be easily oxidized into the expected sulfoxides 6. The menthyloxy and phenyl-8-menthyloxy sulfides 4b,c and sulfoxides 6b,c have been prepared.
