Recueil des Travaux Chimiques des Pays-Bas · 1972 · 37 citations · 8 references
Natural SciencesChemistryGreen ChemistryInorganic ChemistryOrganic ChemistryAddition ReactionsHeterocyclic ChemistryHeterocyclic CompoundsCycloaddition ReactionsSulfur Containing Organic Compounds
Abstract The cyclo‐addition reaction of sulfines with 1,3‐dienes is described. In all cases studied six‐membered ring sulfoxides were formed (Schemes I, II and III). Sulfines with electron‐withdrawing substituents, such as dichlorosulfine, appeared to be very reactive dienophiles. The stereochemistry of the reaction was studied with Z ‐ and E ‐chloro‐phenylsulfine and 2,3‐dimethyl‐1,3‐butadiene. The results show that the stereochemical configuration of the starting sulfine is predominantly retained in the (2 + 4) cyclo‐adduct.
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