Rearrangement reactions of 1,1-divinyl-2-phenylcyclopropanes.
J Am Chem Soc
; 137(1): 322-7, 2015 Jan 14.
Article
en En
| MEDLINE
| ID: mdl-25530073
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.
Texto completo:
1
Bases de datos:
MEDLINE
Asunto principal:
Ácidos
/
Compuestos de Vinilo
/
Ciclopropanos
/
Ésteres
/
Amidas
Idioma:
En
Revista:
J Am Chem Soc
Año:
2015
Tipo del documento:
Article
País de afiliación:
Estados Unidos