73194-80-6Relevant academic research and scientific papers
Ortho-lithium/magnesium carboxylate-driven aromatic nucleophilic substitution reactions on unprotected naphthoic acids
Aissaoui, Regadia,Nourry, Arnaud,Coquel, Ariane,Dao, Thi Thanh Ha,Derdour, Aicha,Helesbeux, Jean-Jacques,Duval, Olivier,Castanet, Anne-Sophie,Mortier, Jacques
experimental part, p. 718 - 724 (2012/02/16)
Substitution of an ortho-fluoro or methoxy group in 1- and 2-naphthoic acids furnishing substituted naphthoic acids occurs in good to excellent yields upon reaction with alkyl/vinyl/aryl organolithium and Grignard reagents, in the absence of a metal catalyst without the need to protect the carboxyl (CO 2H) group. This novel nucleophilic aromatic substitution is presumed to proceed via a precoordination of the organometallic with the substrate, followed by an addition/elimination.
Synthetic Routes to Benzanthracenes via Transient 1-Benzylisobenzofuran Derivatives
Smith, James G.,Welankiwar, Sudha S.,Chu, Noreen G.,Lai, Eric H.,Sondheimer, Susan J.
, p. 4658 - 4662 (2007/10/02)
A synthetic route to 7-acetoxybenzanthracenes is described based on the generation of 1-benzylisobenzofurans and their capture with methyl acrylate in a Diels-Alder reaction.The 1,4-epoxy-1,2,3,4-tetrahydronaphthalene derivatives so formed are aromatized to naphthoate esters under acidic conditions and hydrolyzed to the naphthoic acids, and these are cyclized to the 7-acetoxybenzanthracenes with zinc chloride in acetic anhydride.
Synthetic Routes to Derivatives of Polycyclic Aromatic Hydrocarbons Using Isobenzofurans as Transient Reactive Intermediates
Smith, James G.,Welankiwar, Sudha S.,Shantz, Barry S.,Lai, Eric H.,Chu, Noreen G.
, p. 1817 - 1824 (2007/10/02)
The known equilibrium between the tautomers benzalphthalan (1) and 1-benzylisobenzofuran (2) has been exploited as a synthetic route to novel substituted polycyclic aromatic compounds.The isobenzofuran was captured in a series of Diels-Alder reactions to
