102058-95-7Relevant academic research and scientific papers
Stereoselective Synthesis and Diels-Alder Reactions of (Z)- and (E)-1,2-Bis(phenylthio)-1,3-butadiene
Chou, Shang-Shing P.,Sun, Der-Jen,Tai, Hai-Ping
, p. 809 - 814 (2007/10/03)
Bromination of 3-phenylthio-2-sulfolene (2) with N-bromosuccinimide gave 2-bromo-3-phenylthio-2-sulfolene (3) which was converted mainly to 2,3-bis(phenylthio)-2-sulfolene (4) by treatment with sodium phenylthiolate.Thermal desulfonylation of 4 at different temperatures in the presence of a base (DBU) yielded stereoselectively the (Z)- and (E)-1,2-bis(phenylthio)-1,3-butadiene (6).These two geometric isomers could be thermally interconverted.The Diels-Alder reactions of 6 were also investigated.Only the (Z)-diene 6a could undergo the Diels-Alder reaction; the (E)-diene 6b was in situ converted to the Z isomer before undergoing the Diels-Alder reactlon.The reaction of 6a with N-phenylmaleimide gave the cycloaddition product 7 with complete endo selectivity, but under daylight or during chromatography it readily underwent a thioallylic rearrangement to yield 8 with inversion of configuration.The cycloaddition of 6a with methyl acrylate proceeded regiospecifically, but generating a mixture of endo and exo isomers.The endo/exo ratio could be increased by using ZnCl2 as the catalyst.Key Words: 1,2-Bis(phenylthio)-1,3-butadiene; Stereoselective synthesis; Diels-Alder reactions
Preparation of 2,3-Dihetero-Substituted 1,3-Dienes from Brominated 2-Sulfolenes
Chou, Ta-shue,Lee, Shwu-Jiuan,Peng, Man-Li,Sun, Der-Jen,Chou, Shang-Shing Peter
, p. 3027 - 3031 (2007/10/02)
A general procedure for the preparation of 2,3-dihetero-substituted 1,3-butadienes is described.These dienes are obtained from the thermolysis of the corresponding 3,4-disubstituted 3-sulfolenes, which can be prepared by nucleophilic substitution reaction
SYNTHESIS AND DIELS-ALDER REACTIONS OF 2,3-BIS(BENZENETHIO)-1,3-BUTADIENE
Lucchi, Ottorino de,Marchioro, Gaetano
, p. 305 - 310 (2007/10/02)
Two different routes to the preparation of 2,3-bis(benzenethio)-1,3-butadiene (1) are reported.Diene 1 is shown to react with maleic anhydride, (E)-1,2-bis(benzenesulfonyl)ethylene and 4-phenyl-1,2,4-triazoline-3,5-dione to give the respective Diels-Alder
