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Course of cyclization of dienols, polyenes, and dienyne mediated by mercuric salts were controlled by stability of cationic intermediates and source of mercuric salts. Reaction of (E)-5,9-dimethyl-4,8-decadiene-1-ol with mercuric acetate gave the intramolecular oxymercuration product, whereas one with mercuric triflate produced the olefin cyclization products.
Novel condensation of ketones with homoallyl alcohols catalyzed by Hg(OTf) 2 has been developed, generating a 6-membered ring ether alcohol, bisether, and olefins. The reaction is initiated by hemiacetal formation, and cyclization of the resulting oxonium cation provides the 6-membered ring carbocation as a common intermediate. Thus, it is a catalytic Prins-type condensation of non-activated...
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