Radical and Ionic Reactions of (Benzoylmethyl)mercurials

Article abstract of DOI:10.1021/jo00290a050

Photolysis of PhCOCH2HgCl or (PhCOCH2)2Hg yields benzoylmethyl radicals which can be trapped by anions such as Me2C=NO2^-, RC(CO2Et)2^-, RC(O^-)=CH2 or by other electron-rich systems such as (RO)3P, N-methylpyrrole, enamines, or norbornene.Electron transfer from the adduct radicals to the mercurials yields PhCOCH2A from the anions A^-, PhCOCH2P(O)(OR)2 from P(OR)3, and the phenacyl derivative from N-methylpyrrole or enamines.Easily oxidized anions such as PhCOCPh2^- or PhC(CH3)=NO2^- react with PhCOCH2^* by electron transfer to yield the dimer derived from the anion.Addition of PhCOCH2^* to norbornene yields a substituted 3-benzoylpropyl radical which cyclizes at the ortho position of the benzoyl group to give the α-tetralone derivative.