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Acid‐dependent Divergent Conversion of ortho‐Arylcyclopropanecarbonyl Carboxaldehydes for the Synthesis of Furanodibenzocycloheptenes and Dibenzocycloheptenes

Von Wiley-VCH zur Verfügung gestellt

Utilization of the donor-acceptor chemistry of cyclopropane is demonstrated for chemoselective cyclization to generate either furanodibenzocycloheptene or dibenzocycloheptene analogs depending on the choice of acids, catalytic NHTf2 or stoichiometric (+)-CSA, in reacting with ortho-arylcyclopropanecarbonyl carboxaldehyde substrates.


Abstract

ortho-Arylcyclopropanecarbonyl carboxaldehydes were utilized common substrates for the synthesis of furanodibenzocycloheptenes and dibenzocycloheptenes. Excess amount of (+)-camphorsulfonic acid ((+)-CSA) could lead to acid-promoted cyclopropane ring opening/cyclization reaction of the common substrates to give dibenzocycloheptene products in up to 87% yield. Alternatively, when the common precursors were treated with catalytic amount of super acid (NHTf2) resulting in the formation of furanodibenzocycloheptenes as a mixture of two regioisomeric products.

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