7218-21-5Relevant articles and documents
Novel one-pot synthesis of acetoxy-2,4-cyclohexadienones
Deota, Pradeep T.,Upadhyay, Piyush R.,Parmar, Hemant S.
, p. 1715 - 1723 (2007/10/03)
A new, simple, one-pot method for the oxidative acetylation of some substituted phenols leading to acetoxycyclohexa-2,4-dienones is described. A novel diacetoxycyclohexadienone 12 has also been prepared using the present method from 2-hydroxymethyl phenol (salicyl alcohol). Copyright Taylor & Francis, Inc.
?4s+?2s Cycloaddition: Synthesis, Structure and Oxa-di-? Rearrangement of Tricyclo2,6>undecadienones
Singh, Vishwakarma,Raju, Bhupathiraju N.S.,Deota, Pradeep T.
, p. 301 - 304 (2007/10/02)
A simple and efficient synthesis of tricyclo2,6>undecadienones (8-15) is described.The synthesis involves(i) Diels-Alder reaction of a cyclohexadienone (3) and various dienes (4-7) to furnish the keto-acetates (8-11) and (ii) base hydrolysis of 8-11 to the corresponding keto-alcohols (12-15).Photochemical oxa-di-? rearrangement of the cycloadducts (12,13, and 15) to linearly fused polyquinanes (16-18) is also described.The cycloadduct (14) fails to undergo rearrangement possibly due to quenching effect of dienic moiety in the annulated cyclopentene ring.
The stereochemistry and regiochemistry of Diels-Alder reactions of 6-acetoxy-2,6-dimethyl-2,4-cyclohexadienone
Auksi, Hillar,Yates, Peter
, p. 2510 - 2517 (2007/10/02)
6-Acetoxy-2,6-dimethyl-2,4-cyclohexadienone (1) and maleic anhydride in boiling benzene give a single adduct, exo-5-acetoxy-1,5-dimethyl-6-oxobicyclooct-7-ene-endo-2,3-dicarboxylic acid anhydride (2).With propiolic acid 1 gives exo-5-hydroxy-1,5-dimethyl-6-oxobicycloocta-2,7-diene-2-carboxylic acid (15).The high stereoselectivity and regioselectivity of these reactions is interpretable in terms of orbital overlap, closed-shell repulsion, steric, and van der Waals-London effects.