Cascade Radical Reactions via α-(Arylsulfanyl) imidoyl Radicals: Competitive [4+ 2] and [4+ 1] Radical Annulations of Alkynyl Isothiocyanates with Aryl Radicals §

…, R Leardini, M Minozzi, D Nanni…

Index: Leardini, Rino; Nanni, Daniele; Pedulli, Gian Franco; Tundo, Antonio; Zanardi, Giuseppe Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1986 , p. 1591 - 1594

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Citation Number: 42

Abstract

Aryl radicals react with 2-(2-phenylethynyl) phenyl isothiocyanate through a novel radical cascade reaction entailing formation of α-(arylsulfanyl) imidoyl radicals and affording a new class of compounds, ie thiochromeno [2, 3-b] indoles. These derivatives are formed as mixtures of substituted analogues arising from competitive [4+ 2] and [4+ 1] radical annulations. The isomer ratio is strongly dependent on the aryl substituent and is ...