57899-12-4Relevant academic research and scientific papers
Selective Demethylative Cyclisation of 2-Methoxy-allylbenzenes
Devakumar, C.,Mukerjee, S. K.
, p. 368 - 372 (2007/10/02)
Treatment of 3-substituted 2-methoxyallylbenzenes with dry HBr in CHCl3 causes selective demethylative cyclisation to give 7-substituted 2-methyl-2,3-dihydrobenzofurans.The reaction involves mutual participation of allyl and 2-methoxyl groups and is sterically accelerated by substituents vicinal to OCH3.The reaction does not take place in high dielectric solvents such as DMF or DMSO.A propable mechanism envisaging a non-classical ionic transition state is proposed and the synthetic utility of this reaction is also demonstrated.
