Published January 1, 2015 | Version v1
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Pyrrolidine catalyzed reactions of cyclopentadiene with alpha,beta-unsaturated carbonyl compounds.: 1,2-versus 1,4-additions

  • 1. Uludag Univ, Dept Chem, TR-16059 Bursa, Turkey
  • 2. Virginia Commonwealth Univ, Dept Chem, Richmond, VA 23284 USA
  • 3. San Francisco State Univ, Dept Chem & Biochem, San Francisco, CA 94132 USA

Description

A systematic study of the reactions of cydopentadiene with alpha,beta-unsaturated carbonyl compounds in the presence of catalytic pyrrolidine-H2O revealed that the reactions can either proceed with a Michael attack at the beta-carbon of enone, or 1,2-addition to the carbonyl, leading either to 4-cyclopentadienyl-2-butanones or 6-vinylfulvenes. The former can be isolated and/or converted to the corresponding 1,2-dihydropentalenes with base (or in one-pot at longer reaction times). Substitution pattern on the enones on the competing pathways have been studied and consistent mechanisms are proposed. (C) 2015 Elsevier Ltd. All rights reserved.

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