Liebigs Annalen der Chemie · 1992 · 31 citations · 5 references
Natural SciencesChemistryCatalysisGreen ChemistryOrganic ChemistryHeterocycle SynthesisHeterocyclic ChemistryHeterocyclic CompoundsOrganic SynthesisRegioselectivity In CycloadditionsRing-forming Reactions
Abstract The regioselectivity in cyclofunctionalization of some acyclic olefinic alcohols with benzeneselenenyl halides (PhSeCl and PhSeBr) at different temperatures (−78 ° C, O ° C and room temperature) is investigated. It has been found that Δ 4 ‐ and Δ 5 ‐ alkenols are converted into five‐ and/or six‐membered cyclic phenyl selenoethers, the yield of which decreases with increasing reaction temperature. PhSeCl has been found to be more efficient than PhSeBr in the cyclization reactions.
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