The in-bicyclo [4.4. 4]-1-tetradecyl cation: a stable substance with a three-center, two-electron carbon-hydrogen-carbon bond

JE McMurry, T Lectka, CN Hodge

Index: McMurry; Lectka; Hodge Journal of the American Chemical Society, 1989 , vol. 111, # 24 p. 8867 - 8872

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Citation Number: 55

Abstract

Abstract The synthesis of the title cation 3 is presented, and evidence is amassed to show that the substance contains a three-center, two-electron CHC bond. Among the evidence obtained is the'H NMR spectrum of 3, which shows a one-proton resonance for the CHC hydrogen at b-3.46 with a coupling constant JC+= 47 Hz. Upon substitution of the inside hydrogen by deuterium, the corresponding CDC bridged cation shows an upfield shift to 6 ...