59951-64-3Relevant academic research and scientific papers
Iron-Catalyzed Synthesis of Tetrahydronaphthalenes via 3,4-Dihydro-2H-pyran Intermediates
Watson, Rebecca B.,Schindler, Corinna S.
supporting information, p. 68 - 71 (2018/01/17)
The development of an iron(III)-catalyzed synthetic strategy toward functionalized tetrahydronaphthalenes is described. This approach is characterized by its operational simplicity and is distinct from currently available procedures that rely on [4 + 2]-cycloadditions. Our strategy takes advantage of the divergent reactivity observed for simple aryl ketone precursors to gain exclusive access to tetrahydronaphthalene products (23 examples). Detailed mechanistic investigations identified pyrans as reactive intermediates that afford the desired tetrahydronaphthalenes in high yields upon iron(III)-catalyzed Friedel-Crafts alkylation.
Gold-catalyzed reactions of enynals/enynones with norbornenes: Generation and trapping of cyclic o-quinodimethanes (o-QDMs)
Zhu, Shifa,Zhang, Zhicai,Huang, Xiaobing,Jiang, Huanfeng,Guo, Zhengjiang
, p. 4695 - 4700 (2013/05/09)
Fan-like structures: An efficient AuIII-catalyzed method to generate the highly reactive cyclic o-quinodimethane (o-QDM) species from easily available enynals or enynones is presented (see scheme). This method produced a variety of structurally unique fan-like products with the advantages of mild reaction conditions, excellent diastereoselectivities, and high functional-group tolerance. Copyright
The synthesis and chemistry of 1,3-bridged polycyclic cyclopropenes: 8-Oxatricyclo[3.2.1.02,4]octa-2,6-dienes
Lee, Gon-Ann,Chang, Chih-Yi,Cherng, Chih-Hwa,Chen, Chi-Sheng,Liu, Mei
, p. 839 - 845 (2007/10/03)
Three 1,3-bridged polycyclic cyclopropenes, exo-8-oxatricyclo[3.2.1.0 2,4]octa-2,6-diene (10), endo-8-oxatricyclo[3.2.1.0 2,4]octa-2,6-diene (11), and exo-6,7-benzo-1,5-diphenyl-8- oxatricyclo[3.2.1.02,4]octa-2,6-diene (12), have been synthesized by elimination of 2-chloro-3-trimethylsilyl-8-oxatricyclo[3.2.1.0 2,4]-oct-6-enes, 17,18 and 30, which were generated from 1-chloro-3-trimethylsilylcyclopropene with furan and diphenylisobenzofuran. We have demonstrated a facile route to synthesize the highly strained 1,3-fused polycyclic cyclopropenes, 10, 11, and 12. The stereochemistry of the Diels-Alder reactions of cyclopropene 16 with furan and DPIBF are different. Cyclopropene 16 was treated with furan to form exo-exo and endo-exo adducts (5:2) and treated with DPIBF to generate an exo-exo adduct. Compounds 10, 11 and 12 undergo isomerization reactions to form benzaldehyde and phenyl 4-phenyl-[1]naphthyl ketone to release strain energies via diradical mechanisms.
