(3 + 3)-Cyclodimerization of donor-acceptor cyclopropanes. Three routes to six-membered rings

J Org Chem. 2011 Nov 4;76(21):8852-68. doi: 10.1021/jo201612w. Epub 2011 Oct 5.

Abstract

The ability of donor-acceptor cyclopropanes to (3 + 3)-cyclodimerize is disclosed. It has been found that Lewis acid-induced transformations of 2-(hetero)arylcyclopropane-1,1-dicarboxylates containing electron-abundant aromatic substituents led to the construction of six-membered cyclic systems. Depending on the substrate properties and the Lewis acid applied, three types of products can be obtained: (1) 1,4-diarylcyclohexanes, (2) 1-aryl-1,2,3,4-tetrahydronaphthalenes, and (3) 9,10-dihydroanthracenes.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anthracenes / chemistry
  • Cyclization
  • Cyclohexanes / chemistry
  • Cyclopropanes / chemistry*
  • Electrons
  • Molecular Structure
  • Stereoisomerism

Substances

  • Anthracenes
  • Cyclohexanes
  • Cyclopropanes