- “TPG-lite”: A new, simplified “designer” surfactant for general use in synthesis under micellar catalysis conditions in recyclable water
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Using the oxidized, carboxylic acid-containing form of MPEG-750, esterification with racemic vitamin E affords a new surfactant (TPG-lite) that functions as an enabling, nanoreactor-forming amphiphile for use in many types of important reactions in synthesis. The presence of a single ester bond is suggestive of simplified treatment as a component of (eventual) reaction waste water, after recycling. Many types of reactions, including aminations, Suzuki-Miyaura, SNAr, and several others are compared directly with TPGS-750-M, leading to the conclusion that TPG-lite can function as an equivalent nanomicelle-forming surfactant in water. Prima facie evidence amassed via DLS and cryo-TEM analyses support these experimental observations. In silico evaluations of the aquatic toxicity and carcinogenicity of TPG-lite indicate that it is safe to use.
- Thakore, Ruchita R.,Takale, Balaram S.,Hu, Yuting,Ramer, Selene,Kostal, Jakub,Gallou, Fabrice,Lipshutz, Bruce H.
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- A Novel Synthesis of cis-Dihydro-rose Oxide and Related Stereochemistry
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A new synthesis of cis-dihydro-rose oxide from elsholtzia oil is presented.The stereochemistry of catalytic hydrogenation of elsholtziol is discussed, and configurations of the diastereoisomers of the resulting tetrahydroelsholtziol have been deduced with the aid of gas chromatography, infrared spectroscopic analysis and conformational analysis.Stereochemical study of catalytic dehydration of tetrahydroelsholtziols indicates that the dehydration-rearrangement reactions follow a trans-elimination process.
- Liu, Chu-tsin,Chang, Chi-hsien,Chou, Tsu-liang
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p. 129 - 132
(2007/10/02)
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- Reaction of Acetals with Grignard Reagents
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The reaction of dialkyl acetals derived from α,β-unsaturated aldehydes with Grignard reagents using TiCl4 in THF afforded the cross coupling products, allyl ethers, in high yields.The TiCl4-promoted reaction of alkyl 2,4-dichlorophenyl acetals, synthesized from 3,4-dihydro-2H-pyran or ethyl vinyl ether and 2,4-dichlorophenol, with Grignard reagents in THF at low temperature afforded the corresponding unsymmetrical ethers in high yields.When alkyl 2,4-dichlorophenyl acetals, synthesized from aromatic aldehyde or vinyl ethers and 2,4-dichlorophenol, were treated with Grignard reagents in benzene or toluene at room temperature in the absence of TiCl4, the cross coupling reaction took place and the corresponding ethers were isolated in good yields.
- Ishikawa, Hiroshi,Mukaiyama, Teruaki,Ikeda, Shigeru
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p. 776 - 780
(2007/10/02)
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