(2,7-Disubstituted-1,8-biphenylenedioxy)bis(dimethylaluminum) as Bidentate Organoaluminum Lewis Acids: Elucidation and Synthetic Utility of the Double Electrophilic Activation Phenomenon was written by Ooi, Takashi;Takahashi, Makoto;Yamada, Masao;Tayama, Eiji;Omoto, Kiyoyuki;Maruoka, Keiji. And the article was included in Journal of the American Chemical Society in 2004.Synthetic Route of C12H17NO2 This article mentions the following:
A series of complexes I [R = Me, Me2CH, Ph, cyclohexyl, n-octyl, 3,5-(Me3C)2C6H3] has been readily prepared in situ by treatment of the requisite 2,7-disubstituted 1,8-biphenylenediols II, readily available from inexpensive m-anisidine, with Me3Al (2 equiv) in CH2Cl2 at room temperature Evaluation of complexes I as bidentate organoaluminum Lewis acids has been performed by the reduction of ketonic substrates, such as 5-nonanone and acetophenone, using Bu3SnH as a hydride source in comparison to the conventional monodentate Lewis acid dimethylaluminum 2,6-xylenoxide, uncovering the significantly high activation ability of I toward carbonyl. Particularly, I (R = Me) exerted the highest reactivity, which has also been emphasized in the Mukaiyama aldol reaction. The structure of the bidentate Lewis acids I was unambiguously determined by single-crystal X-ray diffraction anal. of I [R = 3,5-(Me3C)2C6H3] possessing bulky di-tert-butylphenyl substituents, revealing the rigid dimeric assembly in the solid state. The double electrophilic activation of carbonyl substrate by I (R = Me) has been supported by low-temperature 13C NMR anal. as well as theor. study using the Gaussian 98 program. Moreover, unique stereoselectivity has been observed in the I (R = Me)-promoted Mukaiyama Michael addition, and highly chemoselective functionalization of carbonyl compounds in the presence of their acetal counterparts has been realized using I (R = Me). Finally, the effectiveness of I (R = Me) for the activation of ether functionality has been demonstrated in the Claisen rearrangement of allyl vinyl ethers. In the experiment, the researchers used many compounds, for example, N-(3-Methoxyphenyl)pivalamide (cas: 56619-93-3Synthetic Route of C12H17NO2).
N-(3-Methoxyphenyl)pivalamide (cas: 56619-93-3) belongs to ethers. Relative to alcohols, ethers are generally less dense, are less soluble in water, and have lower boiling points. They are relatively unreactive, and as a result they are useful as solvents for fats, oils, waxes, perfumes, resins, dyes, gums, and hydrocarbons. Vapours of certain ethers are used as insecticides, miticides, and fumigants for soil. At room temperature, ethers are pleasant-smelling colourless liquids. Relative to alcohols, ethers are generally less dense, are less soluble in water, and have lower boiling points. They are relatively unreactive, and as a result they are useful as solvents for fats, oils, waxes, perfumes, resins, dyes, gums, and hydrocarbons. Vapours of certain ethers are used as insecticides, miticides, and fumigants for soil.Synthetic Route of C12H17NO2
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem