Carbenoid-mediated nucleophilic “hydrolysis” of 2-(dichloromethylidene)-1, 1, 3, 3-tetramethylindane with DMSO participation, affording access to one-sidedly …

R Knorr, T Menke, J Freudenreich…

Index: Knorr, Rudolf; Pires, Claudio; Freudenreich, Johannes Journal of Organic Chemistry, 2007 , vol. 72, # 16 p. 6084 - 6090

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Abstract

Abstract 2-(Dichloromethylidene)-1, 1, 3, 3-tetramethylindane was “hydrolyzed” by solid KOH in DMSO as the solvent at≥ 100 C through an initial chlorine particle transfer to give a Cl, K-carbenoid. This short-lived intermediate disclosed its occurrence through a reversible proton transfer which competed with an oxygen transfer from DMSO that created dimethyl sulfide. The presumably resultant transitory ketene incorporated KOH to afford the ...