Carbethoxynitrene. Stereochemistry of the intermolecular singlet carbon-hydrogen insertion

JM Simson, W Lwowski

Index: Simson,J.M.; Lwowski,W. Journal of the American Chemical Society, 1969 , vol. 91, p. 5107 - 5113

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Citation Number: 12

Abstract

Abstract: Carbethoxynitrene inserts into the CH bonds of 3-methylhexane with a selectivity that does not change over a concentration range from 100 to 1.2 mol% of the hydrocarbon. The selectivity is also unaffected by the presence of a triplet nitrene trap, a-methylstyrene, and by using a heavy atom solvent, dibromomethane, instead of dichloromethane. The insertion into the tertiary CH bond of optically active 3-methylhexane proceeds with 100% ...