Preparation of phenanthrenes by photocyclization of stilbenes containing a tosyl group on the central double bond. A versatile approach to the synthesis of phenanthrenes and phenanthrenoids.
We have developed a useful modification of the classical preparation of phenanthrenes by UV irradiation of stilbenes in the presence of an oxidant. This modification involves the irradiation, in the presence of base, of stilbenes possessing a sulfonyl group linked to the central double bond. We have proved that this protocol can be successfully applied for the synthesis of diverse phenanthrenes and phenanthrenoids.
Neo
Ana G
AG
Departamento de Química Orgánica y Unidad Asociada al C.S.I.C., Universidad de Santiago de Compostela, 15782-Santiago de Compostela, Spain.
López
Carmen
C
Romero
Victor
V
Antelo
Berta
B
Delamano
José
J
Pérez
Antonio
A
Fernández
Dolores
D
Almeida
Jesús F
JF
Castedo
Luis
L
Tojo
Gabriel
G
D003500:Cyclization; D015394:Molecular Structure; D010616:Phenanthrenes / Q000138:chemical synthesis* / Q000737:chemistry; D010777:Photochemistry; D013237:Stereoisomerism; D013267:Stilbenes / Q000737:chemistry*
D010616:Phenanthrenes; D013267:Stilbenes