594822-16-9Relevant academic research and scientific papers
Ruthenium(II) Complexes with η6-Coordinated 3-Phenylpropanol and 2-Phenylethanol as Catalysts for the Tandem Isomerization/Claisen Rearrangement of Diallyl Ethers in Water
Lastra-Barreira, Beatriz,Francos, Javier,Crochet, Pascale,Cadierno, Victorio
supporting information, p. 3465 - 3474 (2018/10/31)
A series of half-sandwich ruthenium(II) complexes containing η6-coordinated 2-phenylethanol and 3-phenylpropanol ligands, namely [RuCl2{η6-C6H5CH2(CH2)nCH2OH}(PR3)] (PR3 = PMe3, PPh3, P(OMe)3, P(OEt)3, P(OiPr)3, P(OPh)3; n = 0 (1a-f), 1 (2a-f)), have been investigated as catalysts for the tandem isomerization/Claisen rearrangement of diallyl ethers into γ,δ-unsaturated aldehydes using, for the first time, water as solvent. The best results in terms of activity and regioselectivity were obtained with the 3-phenylpropanol derivative [RuCl2(η6-C6H5CH2CH2CH2OH){P(OEt)3}] (2d). Thus, using only 1 mol % of this complex, in combination with NaOH (2 mol %), different diallyl ethers could be conveniently converted into the corresponding aldehydes in high yields and short times under relatively mild thermal conditions (100 °C).
Synthesis of conjugated γ- and δ-lactones from aldehydes and ketones via a vinylation(allylation)-ring closing metathesis-oxidation sequence
Marco, J. Alberto,Carda, Miguel,Rodríguez, Santiago,Castillo, Encarnación,Kneeteman, María N.
, p. 4085 - 4101 (2007/10/03)
Nucleophilic C-vinylation and C-allylation of aldehydes and ketones followed by O-allylation of the obtained carbinols gave the corresponding allyl or homoallyl ethers, respectively. Ring-closing metathesis of these compounds afforded in many cases cyclic ethers (dihydrofurans and dihydropyrans, respectively) bearing disubstituted and trisubstituted C=C bonds. These were then subjected to allylic oxidation to yield conjugated γ- and δ-lactones. Reasons for the observed failures are presented and discussed.
Synthesis of conjugated γ- and δ-lactones from aldehydes and ketones via a vinylation/allylation-ring closing metathesis-oxidation sequence
Carda, Miguel,Castillo, Encarnación,Rodríguez, Santiago,Uriel, Santiago,Marco, J. Alberto
, p. 1639 - 1641 (2007/10/03)
Nucleophilic C-vinylation or C-allylation of aldehydes and ketones followed by O-allylation of the obtained carbinols gave the corresponding allyl ethers. Ring-closing metathesis of the latter afforded cyclic ethers (dihydrofurans and dihydropyrans, respectively) which were then subjected to allylic oxidation to yield conjugated γ- and δ-lactones.
