147919-60-6Relevant articles and documents
Regioselective synthesis of methyl 2,3-dihydro-2-aryl benzofuran-3-carboxylates using thallium(III) nitrate
Khanna,Singh,Garg,Kapoor
, p. 585 - 590 (1993)
Flavanones (1a-d) undergo smooth ring contraction with thallium(III) nitrate in the presence of perchloric acid and trimethyl orthoformate resulting in the formation of methyl 2,3-dihydro-2-arylbenzofuran-3-carboxylates (2a-d) in good yields. The mechanism of this oxidation has also been discussed.
Hypervalent iodine oxidation of flavanones: A new synthesis of methyl 2-aryl-2,3-dihydrobenzofuran-3-carboxylates by 1,2-aryl shift
Prakash,Tanwar
, p. 1168 - 1171 (2007/10/02)
Flavanones (1), on oxidation with (diacetoxyiodo)benzene-sulfuric acid (DIB-H2SO4) or (hydroxy(tosyloxy)iodo)benzene (HTIB) in trimethyl orthoformate, undergo facile ring contraction by 1,2-aryl shift, thereby yielding methyl 2-aryl-2,3-dihydrobenzofuran-3-carboxylates (4) as major products (40-80%). cis-3-Methoxyflavanones (5) and flavones (3) are the minor products formed in variable ratios.