38425-47-7Relevant academic research and scientific papers
Synthesis of Silylated Cyclobutanone and Cyclobutene Derivatives Involving 1,4-Addition of Zinc-Based Silicon Nucleophiles
Cui, Ming,Oestreich, Martin
supporting information, p. 16103 - 16106 (2021/10/12)
A copper-catalyzed conjugate silylation of various cyclobutenone derivatives with Me2PhSiZnCl ? 2LiCl or (Me2PhSi)2Zn ? xLiCl (x≤4) to generate β-silylated cyclobutanones is reported. Trapping the intermediate enolate with ClP(O)(OPh)2 affords silylated enol phosphates that can be further engaged in Kumada cross-coupling reactions to yield silylated cyclobutene derivatives.
-Cycloaddition Reaction of Sulfilimines with Cyclobutenones: Access to Benzazepinones
Xie, Xiaozhou,Sun, Jiangtao
, p. 8921 - 8925 (2021/11/20)
A catalyst-free [4+3]-cycloaddition reaction of N-aryl sulfilimines with cyclobutenones is described, which provides a straightforward protocol for synthesizing 1,5-dihydro-2H-benzo[b]azepin-2-ones under mild reaction conditions. This reaction features a
Enantioselective Synthesis of 4-Hydroxy-dihydrocoumarins via Catalytic Ring Opening/Cycloaddition of Cyclobutenones
Zhang, Hang,Luo, Yao,Li, Dawei,Yao, Qian,Dong, Shunxi,Liu, Xiaohua,Feng, Xiaoming
, p. 2388 - 2392 (2019/03/29)
A highly diastereo- and enantioselective ring-opening/cycloaddition reaction of cyclobutenones with 2-hydroxyacetophenones or salicylaldehyde was achieved by employing a chiral N,N′-dioxide-scandium(III) complex as the catalyst. It provided various 3-phen
Rhodium(i)-catalysed intermolecular alkyne insertion into (2-pyridylmethylene)cyclobutenes
Matsuda, Takanori,Matsumoto, Takeshi
, p. 5023 - 5027 (2016/06/14)
Cyclobutenes with 2-pyridylmethylene groups at the 3 position underwent an intermolecular alkyne insertion reaction in the presence of a rhodium(i) catalyst at 170 °C to afford substituted benzenes. Among the different 2-pyridylmethylene groups examined, 3-methyl-2-pyridyl derivatives showed superior activity and readily coupled with various alkynes, including sterically demanding, heteroaromatic and terminal alkynes.
Regiodivergent cyclobutanone cleavage: Switching selectivity with different Lewis acids
Souillart, Laetitia,Cramer, Nicolai
, p. 1863 - 1867 (2015/01/30)
The exploitation of strain release in small rings as driving force to enable complex transformations is a powerful synthetic tool. Among them, cyclobutanones are particularly versatile substrates that can be elaborated in a wide variety of structurally diverse building blocks. Herein, Lewis acid catalyzed rearrangement reactions are presented that provide selective access to two structurally distinct polycyclic scaffolds, that is, indenylacetic acid derivatives and benzoxabicyclo[3.2.1]octan-3-ones. The choice of the Lewis acid fully controls the reaction pathway and the regioselectivity of the cyclobutanone C-C bond cleavage site.
Rh(II)-catalyzed [2,3]-sigmatropic rearrangement of sulfur ylides derived from N-tosylhydrazones and sulfides
Li, Yuye,Huang, Zhongxing,Wu, Xinhu,Xu, Peng-Fei,Jin, Jing,Zhang, Yan,Wang, Jianbo
, p. 5234 - 5240 (2012/08/07)
In this paper, Rh2(OAc)4-catalyzed [2,3]-sigmatropic rearrangement of sulfur ylides derived from N-tosylhydrazones and sulfides is reported. A series of tosylhydrazones derived from aldehydes were successfully used for [2,3]-sigmatropic rearrangement by reaction with either allylic phenyl sulfides or propargyl phenyl sulfides. The reaction conditions were optimized and afforded the products in moderate to good yields. In addition, a novel and convenient approach for the synthesis of cyclobutenones and cyclopropanes has been developed through direct oxidation of the rearrangement products.
Efficient approach to 1,2-diazepines via formal diazomethylene insertion into the C-C bond of cyclobutenones
Sugimoto, Kenji,Hayashi, Rie,Nemoto, Hideo,Toyooka, Naoki,Matsuya, Yuji
, p. 3510 - 3513 (2012/07/31)
Efficient monocyclic 1,2-diazepine formation via a tandem electrocyclization reaction of cyclobutenones with lithiodiazoacetate is demonstrated. The reaction proceeds through an oxy anion-accelerated 4π-ring opening of cyclobutene followed by an 8π-ring closure of the resultant oxy anion-substituted diazo-diene under mild conditions to furnish a 1,2-diazepine via formal diazomethylene insertion into the C-C bond of cyclobutenone.
New access to a tricyclo[3.2.1.02,7]oct-3-ene structure
Dubarle-Offner, Julien,Marrot, Jér?me,Rager, Marie-No?lle,Le Bideau, Franck,Jaouen, Gérard
, p. 800 - 802 (2007/12/25)
A thermally induced reaction cascade including an electrocyclic rearrangement, two Diels-Alder reactions and a 1,4-elimination from a simple cyclobutene carbonate can explain the synthesis of a complex tricyclo[3.2.1.02,7]oct-3-ene core structu
The intermediacy of oxycyclobutenes in the synthesis and reactions of cyclobutenones and cyclobutenols
Frimer, Aryeh A.,Pizem, Hillel
, p. 12175 - 12186 (2007/10/03)
Vinylcyclobutenol 7, generated via the singlet oxygenation of alkylidenecyclobutene 5, rearranges at room temperature to a solvent dependent mixture of isomeric dienones 10 and 11. Alkylidenecyclobutene 5 was prepared in turn via an inverse Wittig additio
