54764-74-8Relevant academic research and scientific papers
A Novel Photochemical Structural Inversion: The First Methoxy-Hydroxymethyl Isomerization
Westhuizen, Jan H. van der,Ferreira, Daneel,Roux, David G.
, p. 1540 - 1543 (2007/10/02)
Photolysis of 4-methoxybenzofuran-3(2H)-ones provides the first example of structural inversion of an arylmethoxy-group to the corresponding hydroxymethyl function.Suitable structural parameters permit subsequent rearrangement of the heterocyclic ring to 5-hydroxyisochroman-4-ones.By contrast photolysis of the isomeric 4-methoxybenzofuran-2(3H)-one leads directly to the deoxybenzoin analogue.
Flavonoid synthesis based on photolysis of flavan-3-ols, 3-hydroxyflavanones, and 2-benzylbenzofuranones
Fourie, Theunis G.,Ferreira, Daneel,Roux, David G.
, p. 125 - 133 (2007/10/07)
Irradiation of flavan-3-ols, 3-hydroxyflavanones, and 2-benzylbenzofuranones in methanol leads mainly to photochemical opening of the heterocyclic ring, or to its complete photofragmentation, the products being trapped by reaction with the solvent. Fission of exocyclic C-O bonds also occurs, accompanied by intramolecular rearrangements. The course of these reactions is often dependent on the position and nature of substituents. The conversions provide novel routes to 1,3-diaryl-1-methoxypropan-2-ols, 1,3-diaryl-2,2-dimethoxypropan-1-ones, cis-3-methoxyflavanones, isoflavones, flavanones, and trans-chalcones, and hence to α-hydroxychalcones, cis- and trans-α-methoxychalcones, and 2-methoxy-2-(α-methoxybenzyl)benzofuranones.
