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The SmI2-mediated reductions of ketones, imines, and α,β-unsaturated esters have been shown to be instantaneous in the presence of H2O and an amine in THF. The SmI2-mediated reductions are not only shown to be fast and quantitative by the addition of H2O and an amine, but the workup procedures are also simplified. Competing experiments with SmI2/H2O/amine confirmed that α,β-unsaturated esters could be selectively reduced in the presence of ketones or imines. Comparison of analogue ligands showed that nitrogen and phosphorus ligands are superior to oxygen and sulfur ligands in these reductions. The trialkylphosphine 1,2-bis(dimethylphosphino)ethane (DMPE) provided a primary kinetic isotope effect, yielding a kH/kD of 4.5.

The triazene derivative of N-isopropyl-2-amino-1-phenylpropane XIV, synthetized in seven steps from 2-amino-1-phenylpropane (II), enables a rapid, simple and regiospecific preparation of N-isopropyl-2-amino-1-(4-iodophenyl)propane (N-isopropyl-4-iodoamphe

Two reagents reacting avidly with each other in solution are rendered mutually inactive by attaching each to a separate batch of insoluble polymer. Two-stage reactions in which a soluble reagent reacts first with one polymeric reagent and the product with the second polymeric reagent afford advantages over analogous reactions in solution. In acylation reactions of carbon acids, the simultaneous use of a polymeric strong base and a polymeric acylating reagent proved to be superior to the use of soluble reagents, both for bringing about quantitative acylations and for coping with undesirable side reactions. New polymeric strong bases were prepared: polymeric trityllithium, para-substituted trityllithium polymers, and polymeric lithium diisopropylamide. Active esters of polymeric o-nitrophenol and N-1-hydroxybenzotriazole were used as acylation reagents. The scope and limitation of these reactions and their application to general multiphase systems are discussed.