论文信息 - SYNTHESIS AND DIELS—ALDER REACTIONS OF 2,3-BIS(BENZENETHIO)-1,3-BUTADIENE

SYNTHESIS AND DIELS—ALDER REACTIONS OF 2,3-BIS(BENZENETHIO)-1,3-BUTADIENE

Abstract 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)ethyene and 4-phenyl-1,2,4-triazoline-3,5-dione to give the respective Diels-Alder adducts. The adduct to (E)-1,2-bis(benzenesulfonyl)ethylene (4) has been reductively desulfonylated to the bisthioether 7 which was subsequently oxidized to the corresponding bissulfone 8, providing an entry to bis(benzenthio) and bis(benzenesulfonyl) activated molecules.

O. Lucchi | Gaetano Marchioro

[1] L. Paquette,et al. AN INDIRECT METHOD FOR ENGAGING UNACTIVATED ALKENES AS EFFECTIVE DIENOPHILES IN REGIOSELECTIVE DIELS‐ALDER REACTIONS , 2002 .

[2] C. Dell'erba,et al. PHOTOSTIMULATED REACTIONS OF O-BIS(PHENYLSULFONYL)BENZENE DERIVATIVES WITH SODIUM ARENETHIOLATES IN DIMETHYL SULFOXIDE. EVIDENCE FOR COMPETING PATHWAYS INVOLVING A COMMON INTERMEDIATE Σ RADICAL , 1984 .

[3] V. Lucchini,et al. The (Z)- and (E)-1,2-bis(phenylsulfonyl)ethylenes as synthetic equivalents to acetylene as dienophile , 1984 .

[4] W. Okamura,et al. 2,3-Di(phenylsulfinyl)-1,3-butadiene via a double [2,3]-sigmatropic rearrangement of the bis-sulfenate ester of 2-butyne-1,4-diol. , 1982 .

[5] James Ian Grayson,et al. Preparation and Diels-Alder Reactions of Hetero-Substituted 1,3-Dienes , 1981 .

[6] P. Fuchs,et al. Chlorosulfenylation-dehydrochlorination reactions. New and improved methodology for the synthesis of unsaturated aryl sulfides and aryl sulfones , 1978 .

[7] P. Magnus. RECENT DEVELOPMENTS IN SULFONE CHEMISTRY , 1977 .