70340-08-8Relevant academic research and scientific papers
Unexpected migration of a benzoyl group in the intramolecular Wittig reaction of o-acyloxybenzylidenephosphoranes with benzoyl chlorides: One-pot synthesis of isomeric 3-benzoyl-2-phenylbenzofurans
Begala, Michela,Mancinelli, Michele,Delogu, Giovanna Lucia
, (2020/01/28)
The reaction of o-acyloxybenzylidenetriphenylphosphoranes with substituted benzoyl chlorides in an aprotic solvent led, together with the expected 2-phenylbenzofuran, to isomeric 3-benzoyl-2-phenylbenzofuran derivatives. This result formally corresponds to intramolecular migration of the benzoyl group from the ortho oxygen atom to the ylide carbanion via cyclization and ring opening of the starting o-acyloxybenzylidenetriphenylphosphoranes.
Unexpected one-step synthesis of 3-benzoyl-2-phenylbenzofurans under Wittig conditions
Begala, Michela,Caboni, Pierluigi,Matos, Maria Jo?o,Delogu, Giovanna Lucia
, p. 1711 - 1714 (2018/04/10)
The reaction of 2-hydroxybenzyltriphenylphosphonium bromide with substituted benzoyl chlorides under Wittig conditions, led to 2-phenylbenzofuran derivatives 4a–p and the unexpected formation of 3-benzoyl-2-phenylbenzofuran derivatives 5a–p. Benzoyl chlorides possessing electron-withdrawing groups afforded 3-benzoyl-2-phenylbenzofuran derivatives in higher yields than those with electron-donating groups. This reaction represents a simple and regioselective, one-pot route towards the preparation of deactivated 3-benzoyl-2-phenylbenzofuran compounds which are difficult to obtain by the direct acylation of 2-phenylbenzofurans.
A novel photochemical Wittig reaction for the synthesis of 2-aryl/alkylbenzofurans
Ghosh, Somnath,Das, Jhantu
, p. 1112 - 1116 (2011/03/22)
The synthesis of 2-aryl/alkylbenzofurans has been achieved in high yields under photochemical conditions from readily accessible and suitably substituted phosphonium bromides by an intramolecular photochemical Wittig reaction onto aryloxycarbonyl groups.
