title: Rearrangement reactions of 1,1-divinyl-2-phenylcyclopropanes.
abstract: 1,1-Divinyl-2-phenylcyclopropanes are entry points to a rich area of rearrangement chemistry. With N,N-diallyl amide substrates, tandem radical cyclizations can be initiated at room temperature. Warming provides products of pure thermal rearrangements with acids, ester, and amides. These isomerizations give vinylcyclopentenes resulting from divinylcyclopropane rearrangements and more deeply rearranged tricyclic spirolactams resulting from aromatic Cope rearrangements followed by ene reactions. Conversion of the carbonyl group to an alcohol or ether opens retro-ene pathways followed by either tautomerization or Claisen rearrangement.
authors.affiliation: Department of Chemistry, University of Pittsburgh , Pittsburgh, Pennsylvania 15260, United States.
authors.forename: E Ben
authors.initials: EB
authors.lastname: Hay
authors.forename: Hanmo
authors.initials: H
authors.lastname: Zhang
authors.forename: Dennis P
authors.initials: DP
authors.lastname: Curran
mesh_terms: D000143:Acids / Q000737:chemistry*; D000577:Amides / Q000737:chemistry*; D003500:Cyclization; D003521:Cyclopropanes / Q000737:chemistry*; D004952:Esters / Q000737:chemistry*; D005609:Free Radicals / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D013696:Temperature; D014753:Vinyl Compounds / Q000737:chemistry*
chemical_list: D000143:Acids; D000577:Amides; D003521:Cyclopropanes; D004952:Esters; D005609:Free Radicals; D014753:Vinyl Compounds