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Site-selective and regioselective Diels-Alder reaction of allenyl aryl ethers

Matloubi Moghaddam, F ; Sharif University of Technology | 2010

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  1. Type of Document: Article
  2. DOI: 10.1007/s00706-010-0406-1
  3. Publisher: 2010
  4. Abstract:
  5. The site-selectivity and regioselectivity of Diels-Alder reactions of allenyl aryl ethers with cyclopentadiene and acrolein were studied. While cyclopentadiene (as an electron-rich diene) only reacted with the external double bond of allenyl aryl ethers to provide the site-selective normal electron demand Diels-Alder cycloadducts, acrolein (as an electron-deficient diene) reacted with the C1-C2 π bond of allenyl aryl ethers to provide the site- and regioselective hetero-Diels-Alder cycloadducts as exclusive products
  6. Keywords:
  7. Acrolein ; Allenes ; Cycloadditions ; Cyclopentadiene ; Hetero-Diels-Alder ; Solvent-free
  8. Source: Monatshefte fur Chemie ; Volume 141, Issue 12 , 2010 , Pages 1333-1337 ; 00269247 (ISSN)
  9. URL: http://link.springer.com/article/10.1007%2Fs00706-010-0406-1