The interaction of the PTA (PTA = 1,3,5-triaza-7-phosphaadamantane) ruthenium complex trans-[RuCl(2)(PTA)(4)] (trans-1) with visible light in chloroform and in water has been studied at room temperature. The complex trans-1 isomerizes to the cis isomer in CHCl(3) with radiation of lambda > 416 nm (Phi(434 nm) (CHCl(3)) = 0.13 +/- 0.01). The isomerization reaction is reversible as cis-1 is transformed into trans-1 with lambda = 367 nm (Phi(367 nm) (CHCl(3)) = 0.25 +/- 0.02). Irradiation at lambda > 416 nm of a solution of trans-1 in water leads to the cis-isomer complex and to the aqua complex (OC-6-32)-[RuCl(H(2)O)(PTA)(4)]Cl (2Cl) by a photoisomerization and photoaquation reaction (Phi(434 nm) (D(2)O) = 0.27 +/- 0.02). The mole ratio of cis-1 to 2Cl is not dependent on the pH but on the concentration of the products in solution. Isomerization in water is not reversible even if only cis-1 is present in solution. Synthesis and characterization of (OC-6-32)-[RuCl(H(2)O)(PTA)(4)](CF(3)SO(3)) (2CF(3)SO(3)) are also presented.
[AlCl(3) + 2THF] is a new catalytic system for the Diels-Alder cycloaddition under SFC and air atmosphere. By using equimolar amounts of reactants, this catalyst prevents the polymerization of the diene and allows the corresponding adducts to be isolated with high regio- and stereocontrol and in excellent yields. [reaction: see text]
An exceptionally mild acetoxyallylation of aldehydes in water promoted by zinc is reported, using 3-bromo-1-acetoxyprop-1-ene as starting material; simple diastereoselectivity mainly depends on the nature of the aldehyde.
An innovative route to prepare a number of variously substituted new biphenyl derivatives is presented here. The protocol avoids the use of a catalyst, an organic solvent, and dry conditions. [reaction: see text]
A new precursor of a formal 1-hydroxy allyl anion is represented by 3-bromo-1-acetoxy-1-propene, which is synthesized by the ZnCl(2)-catalyzed addition of acetyl bromide to propenal. 3-Bromo-1-acetoxy-1-propene reacts with indium powder in THF to give the corresponding 3-acetoxylated ally indium complex, which regioselectively adds to aldehydes, affording monoprotected 1-en-3,4-diols. Diastereoselectivity mainly depends on the nature of the aldehyde; saturated aldehydes afford anti adducts, whereas the alpha,beta-unsaturated aldehydes preferentially lead to the syn isomers. Reaction: see text.
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