A two-step, stereoselective procedure for the synthesis of nine- and ten-membered carbocycles from readily available phthalates is described. A variety of dialkyl phthalates have been transformed into [6,n]-fused bicyclo systems (n = 5, 6, 7) by a dearomatization/cyclization process and then converted into cyclonona- and cyclodecadienes through a bond cleavage reaction, whereby both processes are promoted by alkaline metals in THF.
A one-pot, enantioselective strategy for the dearomatizationannulation of aromatic diesters to give a range of highly functionalized polycyclic molecules with excellent enantioselectivity is presented. This methodology is based on the reaction of bisenolates, prepared by treating aromatic diesters with trialkyltin lithium reagents, which involves a stanna-Brook rearrangement, with 1,ω-dihaloalkanes and
1,2-Aromatic
diesters can be transformed into strained bridged
polycyclic structures by a two-step procedure consisting of an initial
reductive alkylation promoted by alkaline metals, followed by a reaction
of the resulting unsaturated diesters with Me3SnLi. We
propose that a stanna-Brook rearrangement plays a fundamental role
in the formation of the polycyclic organotin acetals obtained. These
unusual compounds could be further functionalized by tin–lithium
exchange followed by alkylation of the newly formed tertiary carbanion.
Alternatively, dialkylated aromatic hydrocarbons have been prepared
via a decarbonilation reaction promoted by Me3SnLi. 1,4-Aromatic
diesters were reductively dialkylated and then transformed into norbornadienone
derivatives by reaction with Me3SnLi. Several stable dibenzonorbornadienones 41 have been prepared in just two steps starting from anthracene 38. The corresponding naphthalene analogues gave 1,4-dialkylnaphthalenes.
The synthetic protocols described provide access to structures that
are not easily obtained through existing synthetic methodologies.
Luces y sombras de dos paradigmas del americanismo español en la renovación del diálogo hispanoamericano (1909)(1910)(1911)(1912) El americanismo, como doctrina y como movimiento asociativo, 2 logró abrirse paso en el mundo de las ideas y en la opinión pública españo-1 Agradecemos los valiosos comentarios de Pilar Cagiao, directora del proyecto de investigación subvencionado por la Fundación Carolina, "El americanismo en España, 1898-1936: instituciones culturales y proyectos educativos", a Salvador Bernabéu Albert y a Eduardo Rey Tristán.2 En relación con el concepto "americanismo asociativo" y al importante papel de las asociaciones como "agentes operativos" del hispanoamericanismo, seguimos a Sepúlveda Muñoz, Isidro:
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