188307-97-3Relevant academic research and scientific papers
Synthesis of aromatic rings embedded in polycyclic scaffolds by triyne cycloaddition: Competition between carbonylative and non-carbonylative pathways
Salacz, Laura,Girard, Nicolas,Suffert, Jean,Blond, Ga?lle
, (2019)
Cycloadditions have emerged as some of the most useful reactions for the formation of polycyclic compounds. The carbonylative cycloaddition of triynes can lead to carbonylative and non-carbonylative competitive pathways, each leading to the formation of an aromatic ring. We report herein the one-pot synthesis of fully- and unsymmetrically-substituted tetracyclic 6,5,7,5-troponic and 6,5,6,5-benzenoid scaffolds using pre-organized triynes showing the competition between these two pathways.
4-Methyltetrahydropyran (4-MeTHP): Application as an Organic Reaction Solvent
Kobayashi, Shoji,Tamura, Tomoki,Yoshimoto, Saki,Kawakami, Takashi,Masuyama, Araki
, p. 3921 - 3937 (2019/11/11)
4-Methyltetrahydropyran (4-MeTHP) is a hydrophobic cyclic ether with potential for industrial applications. We herein report, for the first time, a comprehensive study on the performance of 4-MeTHP as an organic reaction solvent. Its broad application to organic reactions includes radical, Grignard, Wittig, organometallic, halogen-metal exchange, reduction, oxidation, epoxidation, amidation, esterification, metathesis, and other miscellaneous organic reactions. This breadth suggests 4-MeTHP can serve as a substitute for conventional ethers and harmful halogenated solvents. However, 4-MeTHP was found incompatible with strong Lewis acids, and the C?O bond was readily cleaved by treatment with BBr3. Moreover, the radical-based degradation pathways of 4-MeTHP, THP and 2-MeTHF were elucidated on the basis of GC-MS analyses. The data reported herein is anticipated to be useful for a broad range of synthetic chemists, especially industrial process chemists, when selecting the reaction solvent with green chemistry perspectives.
Synthesis of Functionalized Ring C of Escobarines
Lechuga-Eduardo, Harim,Romero-Ortega, Moises,Olivo, Horacio F.
supporting information, p. 51 - 54 (2016/01/20)
A synthetic strategy was developed for the preparation of α-ethynyl-α,β-epoxy-β-formyl- and α-ethynyl-α,β-epoxy-β-(hydroxymethyl)cyclohexanone from cyclohexenone as a model study in a proposed synthesis of escobarines. This highly functionalized ring is f
Synthesis of highly substituted furans by the electrophile-induced coupling of 2-(1-alkynyl)-2-alken-1-ones and nucleophiles
Yao, Tuanli,Zhang, Xiaoxia,Larock, Richard C.
, p. 7679 - 7685 (2007/10/03)
The coupling of 2-(1-alkynyl)-2-alken-1-ones with nucleophiles, either catalyzed by AuCl3 or induced by an electrophile, provides highly substituted furans in good to excellent yields under very mild reaction conditions. Various nucleophiles, i
