The SRN1 Photoarylation of Indenyl Anions

Article abstract of DOI:10.1021/jo00184a016

Irradiation of Me2SO solutions of indenyl anion and its phenylated analogues in the presence of bromobenzene produces the higher phenylated indenes.Thus indenyl anion (1b) yields 3-phenylindene (3a), 1-phenylindenyl anion (3b) yields 1,3- and 1,1-diphenylindene, 2-phenylindenyl anion (2b) produces 2,3-diphenylindene, 1,3-diphenylindenyl anion (6b) produces 1,1,3- and 1,2,3-triphenylindene, and 1,2-diphenylindenyl anion (5b) produces 1,2,3-triphenylindene (8).In liquid ammonia and tetrahydrofuran more complex reaction pathways are observed.The regiochemistry of phenylation is attributed to radical attack at the most basic site, in accord with a previously published model.