108685-67-2Relevant academic research and scientific papers
Access to Hydroxy-Functionalized Polypropylene through Coordination Polymerization
Cui, Dongmei,Douair, Iskander,Maron, Laurent,Wang, Tiantian,Wu, Chunji,Zhong, Yuanhao
, p. 4947 - 4952 (2020)
Preparation of polyethylenes containing hydroxy groups has been already industrialized through radical copolymerization under harsh conditions followed by alcoholysis. By contrast, hydroxy-functionalized polypropylene has proven a rather challenging goal
A palladium-catalyzed approach to allenic aromatic ethers and first total synthesis of terricollene A
Cui, Yifan,Huang, Chaofan,Li, Can,Lin, Jie,Liu, Qi,Ma, Shengming,Qin, Anni,Shi, Fuchun,Wang, Huanan,Wu, Guolin,Wu, Penglin,Xiao, Junzhe,Xu, Haibo,Yu, Biao,Yuan, Yuan,Zhai, Yizhan,Zheng, Wei-Feng,Zheng, Yangguangyan
, p. 9347 - 9351 (2021/07/25)
A palladium-catalyzed C-O bond formation reaction between phenols and allenylic carbonates to give 2,3-allenic aromatic ethers with decent to excellent yields under mild reaction conditions has been described. A variety of synthetically useful functional
Divergent reactivity of homologue ortho-Allenylbenzaldehydes controlled by the tether length: Chromone versus chromene formation
Alcaide, Benito,Almendros, Pedro,Fernndez, Israel,Del Campo, Teresa Martnez,Naranjo, Teresa
supporting information, p. 1533 - 1541 (2015/01/30)
The divergent behavior of two homologue allenals, namely, 2-(buta-2,3-dienyloxy)- and 2-(propa-1,2-dienyloxy)benzaldehydes, as cyclization substrates is described. 2-(Buta-2,3-dienyloxy)benzaldehydes suffers a formal allenic carbocyclization reaction to afford chromenes, whereas 2-(propa-1,2-dienyloxy)benzaldehydes react to yield chromones. The formation of chromenes is strictly a formal hydroarylation process divided into two parts, namely, allenic Claisen-type rearrangement and oxycyclization. An unknown N-heterocyclic carbene (NHC)-catalyzed allenic hydroacylation reaction must be invoked to account for the preparation of chromones. ortho-Allenylbenzaldehydes bearing either electron-donating substituents or electron-withdrawing substituents worked well to afford both the hydroarylation and hydroacylation products. This unexpected difference in reactivity can be rationalized by means of density functional theory calculations.
Photocycloaddition of arenes and allenes
Streit, Ursula,Birbaum, Frederic,Quattropani, Anna,Bochet, Christian G.
, p. 6890 - 6910 (2013/08/23)
In this work, we report on a new intramolecular para cycloaddition of arenes with allenes, yielding attractive rigid scaffolds bearing several reactive functionalities to build in further diversity. Bicyclo[2.2.2]octadiene- type products and benzoxepine acetals are formed in this reaction, in ratios and yields depending on the substitution pattern on the aromatic ring, the nature of the chromophore, and the tether. This unprecedented reaction has remarkable features that distinguish it from many other photochemical transformations: it is particularly robust with respect to substituents, it can be scaled up without a notable loss of efficiency, and it can lead to structures with a high degree of complexity in low to good yields. All photochemical precursors could be synthesized readily in three steps. We confirmed the compatibility of the nitrogen atom in the photocycloaddition step, which gives access to a bicyclo[2.2.2]octadiene scaffold with two points that allow further diversification. This reaction was scaled up to multigram quantities without erosion of the typically high yields in photocycloadducts. Sequential deprotection of the N- or C-terminus of bicyclic amino acids gave access to two conformationally constrained unnatural amino acids with different dispositions of the two anchor points.
Methods for the preparation of allenes employing indium- and zinc-mediated dehalogenation reactions in aqueous solutions
Lin, Mei-Huey,Tsai, Wen-Shing,Lin, Long-Zhi,Hung, Shiang-Fu,Chuang, Tsung-Hsun,Su, Yi-Jen
, p. 8518 - 8523 (2012/01/19)
Simple and mild methods for the synthesis of allenes, employing indium- and zinc-mediated dehalogenation reactions of vicinal dihalides in an aqueous solvent, are described. By using these procedures, various allenylmethyl aryl ethers and monosubstituted
Synthesis of allenes via CuBr-catalyzed homologation of alk-1-ynes accelerated by microwave
Nakamura, Hiroyuki,Sugiishi, Tsuyuka,Tanaka, Yuko
scheme or table, p. 7230 - 7233 (2009/04/14)
CuBr-catalyzed homologation of alk-1-ynes 1 with paraformaldehyde and N,N-diisopropylamine (or N,N-dicyclohexylamine) was accelerated by microwave irradiation at 150 °C to afford the corresponding allenes 2 in good to high yields in 1-10 min. Bisalkynes 5
Chemistry of gem-Dihalocyclopropanes. XXII. Intramolecular Addition of Cyclopropylidenes to Aliphatic and Aromatic Double Bonds. A Synthesis of 2-Alkenyltropones
Skatteboel, Lars,Nilsen, Nils O.,Myhren, Finn
, p. 782 - 790 (2007/10/02)
Substituted gem-dibromocyclopropanes containing a vinylic or phenolic ether oxygen α to the cyclopropane ring undergo intramolecular cycloaddition as well as ring opening to allenes when treated with methyllithium.Cycloaddition of derivatives with a vinyl
