17404-28-3Relevant academic research and scientific papers
Lithium naphthalenide-induced reductive alkylation and addition of aryl-and heteroaryl-substituted dialkylacetonitriles
Tsao, Jing-Po,Tsai, Ting-Yueh,Chen, I-Chia,Liu, Hsing-Jang,Zhu, Jia-Liang,Tsao, Sheng-Wei
experimental part, p. 4242 - 4250 (2011/02/25)
Lithium naphthalenide (LN)-induced reductive alkylation/addition reactions of aryl-, pyridyl-, and 2-thienyl-substituted dialkylacetonitriles have been investigated. Upon treatment with LN in THF at -40°C, both aryl and pyridyl precursors could undergo the reductive decyanation smoothly, and the in situ generated carbanions could be readily trapped by alkyl halides, ketones, aldehydes, or even oxygen to afford a wide range of functionalized aromatic derivatives bearing a newly established quaternary carbon. To effect the desired reductive alkylation of 2-thienyldialkylacetonitriles, a much lower temperature such as -100°C was required. Also with these substrates, an interesting ring-opening/S-alkylation process was observed when the reductive alkylation were performed at -78°C to give 1-alkylsulfanyl-1,3,4-trienes. A mechanistic discussion is given for this observation.
Nickel(II)-catalyzed carbon-carbon bond formation reaction of functionalized organozinc reagents with aromatic aldehydes
Fu, Ying,Wang, Jin-Xian,Wang, Kehu,Hu, Yulai
experimental part, p. 11124 - 11128 (2009/04/11)
In the presence of a silylating reagent and catalytic amount of Ni(acac)2, organozinc halides reacted with aromatic aldehydes to give the corresponding dialkylation products in good to excellent yields under mild conditions.
The monolayer structure of the branched nonyl phenol oxyethylene glycols at the air-water interface
Green,Su,Lu,Penfold
, p. 1507 - 1515 (2007/10/03)
The behavior of the para-substituted nonyl phenol ethoxylates with branched nonyl chains at the air-water interface was studied to examine the effect of branching in the alkyl chain and the insertion of a benzyl ring in the alkyl chain on the monolayer structure of the nonionic surfactant. A series of para-(C4H9)2CHC6H4(OC2H4)nOH (BNPE), where n=4,8, and 12 were used in the surface tension measurements. The CMC was 1.1 ± 0.3 x 10-5 M for BNPE4, 4.0 ± 0.3 x 10-5 M for BNPE8, and 8.0 ± 0.3 x 10-5 M for BNPE12; the limiting area per molecule (Acmc) at the cmc was 46 ± 3, 61 ± 4, and 75 ± 5 sq A, respectively. For the same size of headgroups, the Acmc values were almost the same as those obtained from dodecyl ethoxylates. This indicated that Acmc for these nonionic surfactants are dependent on the size of headgroups and independent of the chemical structure of the hydrophobic chains. Nonyl phenol layers projected onto the surface normal direction were 18 ± 3 A (BNPE4), 19 ± 3 A (BNPE8), and 22 ± 3 A (BNPE12). These layers, in all cases, were nearly twice as thick as the fully extended chain, suggesting that the hydrophobic chain are widely distributed across the layer an extensive resulting in a strong mixing of the chain with the ethoxylate groups.
Single and double reductive cleavage of C-O bonds of aromatic dimethyl acetals and ketals: Generation of benzylic mono- and dicarbanions
Azzena,Melloni,Pisano,Sechi
, p. 6759 - 6762 (2007/10/02)
The reductive cleavage of aromatic dimethyl acetals and ketals, 1, with Li metal in THF at low temperature allows the generation of stable α-alkoxy-α-arylsubstituted carbanions, avoiding the Wittig rearrangement. Reaction of these carbanions with various electrophiles afforded the expected products 2. Further in situ reaction of compounds 2 afforded the products of reductive electrophilic disubstitution, 3.
