180572-73-0Relevant academic research and scientific papers
Reaction of phosphorus-stabilized carbanions with cyclic enones. Aromatization of the substitution and addition products
Mphahlele, Malose J.,Pienaar, Andre,Modro, Tomasz A.
, p. 1455 - 1460 (2007/10/03)
α-Lithiated alkylphosphonic esters react with substituted cyclohex-2-enones either at the carbonyl group (addition yielding 2-hydroxyalkylphosphonic products) or at the β-carbon (addition-elimination yielding δ-keto phosphonates). Both types of products undergo smooth aromatization when treated with I2 in MeOH or with pyridinium perbromide in AcOH leading to a variety of benzylphosphonic esters substituted in the aromatic ring with the methoxy or hydroxy groups. Mechanisms of the aromatization reactions are discussed.
