936916-72-2Relevant academic research and scientific papers
Ruthenium-catalyzed cascade reactions of diynes with norbornadiene -synthesis of norbornene derivatives
Cheng, Chu-Chun,Change, Chia-Sen,Hsu, Yu-Lin,Lee, Ting-Yu,Chang, Ling-Chueh,Liu, Shih-Hsien,Wu, Yao-Ting
supporting information; experimental part, p. 672 - 679 (2010/03/04)
Norbomene derivatives 7-11 were prepared from norbornadiene and the corresponding diynes by Ru-catalyzed [(2+2)+2] cycloaddition and subsequent transfer hydrogenation. The structure and stereochemistry of the cycloadducts were confirmed by X-ray crystal a
Iridium- and rhodium-catalyzed [2+2+2] cycloadditions of diynes with maleimide: A new synthetic route to highly substituted phthalimides
Alvarez, Leonardo X.,Bessières, Bernard,Einhorn, Jacques
experimental part, p. 1376 - 1380 (2009/04/06)
The [2+2+2] cycloaddition of maleimide with α,ω-diynes in the presence of [IrCl(cod)]2 or [RhCl(cod)]2 and DPPE gives cyclohexadiene derivatives which are readily aromatized with DDQ or MnO 2. This two-step procedure gives
Intramolecular anionic Diels-Alder reactions of 1-aryl-4-oxahepta-1,6-diyne systems in DMSO
Kudoh, Takayuki,Mori, Tomoko,Shirahama, Mitsuhito,Yamada, Masashi,Ishikawa, Teruhiko,Saito, Seiki,Kobayashi, Hisayoshi
, p. 4939 - 4947 (2008/02/03)
Base-promoted cycloaddition reactions of 1-aryl- or 1-aryl-7-substituted-4- oxahepta-1,6-diyne systems in DMSO have proven to involve an anionic intramolecular Diels-Alder process taking place even at room temperature in spite of the reaction suffering from temporary disruption of aromaticity. Although initially formed α-arylallenide anion can be protonated by DMSO, it can be back to the allenide anion probably because of a small acidity difference between α-arylallene and DMSO. The α-arylallenide anion in combination with the α-aryl substituent can constitute an anionic diene structure that undergoes the intramolecular Diels-Alder reaction involving the C(6)-yne part, a very fast process probably because of the increased HOMO-1 level of the anionic diene, as shown by DFT calculations. Diversified substituted naphthalenes, benzofurans, phenanthrenes, and quinolines, including biaryl architectures, are available from 4-oxahepta-1,6-diynes in a highly expeditious way.
