- ESR Spectroscopic Study of Triphenylmethyl-Substituted Thioaminyl Radicals: N-(Triphenylmethylthio)alkylaminyls and -arylaminyls
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The title radicals generated by hydrogen-atom abstraction from the corresponding N-(triphenylmethylthio)-alkylamines and -arylamines, have been studied by means of ESR spectroscopy.The alkylaminyls were transient in solution at room temperature, while the
- Miura, Yozo,Isogai, Mamoru,Kinoshita, Masayoshi
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p. 3065 - 3067
(2007/10/02)
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- Studies on the Preparation and Reactions of Tritylsulfenimines
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Carbonyl compounds react with stable, crystalline triphenylmethanesulfenamide (TrSNH2, 4) under mild conditions to form tritylsulfenimines 5 and 6.Lithiation of acetone tritylsulfenimine (5c) at O deg C led to a novel rearrangement-decomposition producing
- Branchaud, Bruce P.
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p. 3531 - 3538
(2007/10/02)
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- Studies on the Development of the Tritylsulfenyl Group as a Nitrogen Protecting Group and Application in a Synthesis of δ-Coniceine
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The (triphenylmethyl)sulfenyl (tritylsulfenyl, TRS) group was found to posses properties which should make it useful as a nitrogen protecting group.The almost instantaneous reaction of TrSCl (6) with amines produced the corresponding triphenylmethanesulfenamides.The TRS group was found to render the nitrogen atom nonbasic and relatively nonnucleophilic, was stable to aqueous acid, aqueous base, and various reducing agents, and was moderately stable to Moffat oxidation conditions.The TRS group could be cleaved under mild conditions, generating the amine with either CuCl2/EtOH-THF, HI/THF-H2O, or trimethylsilyl iodide (Me3SiI)/CH2Cl2.A synthesis of δ-coniceine (16) illustrates carbon-carbon bond formation with tritylsulfenimine methodology and the utility of the tritylsulfenyl group as a nitrogen protecting group.
- Branchaud, Bruce P.
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p. 3538 - 3544
(2007/10/02)
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