TY - DATA T1 - Synthesis of benzylidenecycloalkan-1-ones and 1,5-diketones under Claisen–Schmidt reaction: Influence of the temperature and electronic nature of arylaldehydes PY - 2017/11/09 AU - Beatriz Lantaño AU - José M. Aguirre AU - Eleonora V. Drago AU - Mariela Bollini AU - Diego J. de la Faba AU - Jorge D. Mufato UR - https://tandf.figshare.com/articles/journal_contribution/Synthesis_of_benzylidenecycloalkan-1-ones_and_1_5-diketones_under_Claisen-Schmidt_reaction_influence_of_the_temperature_and_electronic_nature_of_arylaldehydes/5393320 DO - 10.6084/m9.figshare.5393320 L4 - https://ndownloader.figshare.com/files/9282427 KW - Aldolic condensation KW - benzocycloalkan-1-ones KW - bis-indane-1,5-diketones KW - Michael addition KW - spiropolycyclic-1,5-diketones N2 - Herein, we present the results of the influence of reaction temperature and the electronic nature of arylaldehydes in the reactions of benzocycloalkan-1-ones and arylaldehydes under classical Claisen–Schmidt condensation conditions. The products obtained, 2-arylidene derivatives of benzocycloalkan-1-ones and/or spiropolycyclic-1,5-diketones through multicomponent reactions, depended on the electronic nature of arylaldehyde and the reaction temperature. Besides, under identical conditions, 2-arylideneindan-1-ones afforded bis-indane-1,5-diketones through a process that involves Michael addition reaction, which is also dependent on the temperature. Theoretical studies using density-functional theory allowed understanding the chemical reactivity and the site selectivity of α,β-enones used in this work through the calculation of global and local electrophilicity on C–β. Both the electrophilicity of C-β and the temperature led the course of reaction toward the formation of aldol condensation, aldol condensation/Michael addition, and aldol condensation/dimerization products. This work is the first to perform the structural and configurational assignments of bis-indane-1,5-diketones. ER -