85670-74-2Relevant academic research and scientific papers
Acid-catalysed Cyclization of 2-(3-Methylbut-2-ene)-, 2-(3-Oxobutyl)- and 2-(3-Oxopentyl)-2-methylcyclopentane-1,3-diones
Kasturi, T. R.,Reddy, Madhava
, p. 901 - 906 (2007/10/02)
Novel products isolated from acid-catalysed cyclization reactions of the title compounds (1), (2a) and (2b) with different reagents have been characterized on the basis of their spectral data.The trend of product formation in p-tosic acid-benzene reaction medium remains the same for 1 and 2, irrespective of the nature of substitution in the acyclic component.The role of phenyl substitution in the cyclic part of 1 in guiding the MeOH-HCl promoted bicyclic compound formation is clearly indicated.Diketone (I) without a phenyl substitution yields entirely different products from MeOH-HCl treatment, although the facile enolization of the five-membered ring carbonyl is still reflected in the product formation.Although 2a is reported to yield bicyclic compounds (5c) and (6c) only under delicate reaction conditions, it yields bicyclic compounds as the major products on MeOH-HCl treatment.Thus, the pathway resulting from facile enolization of the five-membered ring carbonyl to afford bicyclooctane-6,8-dione systems under this condition is demonstrated with compounds that are normally known to give normal annelation products on moderate acid treatment.
