86-73-7Relevant articles and documents
Synthesis and thermal rearrangement of pentacyclo[6.5.0.04,12.05,10.09,13]trideca-2,6-diene
Marchand,Rajapaksa,Vidyasagar,Eckrich,Kumar
, p. 11937 - 11944 (1995)
Pentacyclo[6.5.0.04,12.05,10.09,13]trideca-2,6-diene (16) has been synthesized in five steps from 1-hydroxyhexacyclo[6.5.0.02,6.03,11.05,10.09,12]trideca n-7-one (10). Compound 16 undergoes thermal rearrangement to pentacyclo[7.4.0.02,6.03,11.05,10]trideca-7,12-diene (i.e. '[2.2.1]triblattadiene', 19). The intermediacy of cis,cisoid,cis-tricyclo[7.4.0.02,7[trideca-3,5,10,12-tetraene (18) in the thermal rearrangement of 16 was inferred via analysis of the 1H NMR spectrum of partially rearranged 16 and subsequently was further established via the results of a trapping experiment (i.e., fluorene was produced when thermal rearrangement of 16 was performed in the presence of 10% Pd/C).
Hydrogenation of 9-pyridylmethylene- and 9-benzylidene(aza)fluorenes in the presence of rhenium heptasulfide
Kolyadina,Soldatenkov,Ryashentseva,Prostakov
, p. 171 - 173 (1996)
Hydrogenation of 9-pyridylmethylene(aza)fluorenes and 9-benzylidene-4-azafluorene at 250°C and pH2 = 130 atm in the presence of Re2S7 as a catalyst occurs preferably at the exocyclic double bond of the fulvene fragment to yield pyridyl-9-(aza)fluorenylmethanes.
Surface confined ketyl radicals via samarium(II)-grafted mesoporous silicas [3]
Nagl, Iris,Widenmeyer, Markus,Grasser, Stefan,Koehler, Klaus,Anwander, Reiner
, p. 1544 - 1545 (2000)
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Palladium-Catalyzed Coupling of Biphenyl-2-yl Trifluoromethanesulfonates with Dibromomethane to Access Fluorenes
Pan, Shulei,Zhang, Yanghui,Zhu, Qiongqiong
, (2022/03/27)
A facile and efficient method has been developed for the synthesis of fluorenes by Pd-catalyzed C-H alkylation of biphenyl-2-yl trifluoromethanesulfonates. The trifluoromethanesulfonates are more readily available and more environmentally benign than biphenyl iodides, and are advantageous substrates for traceless directing-groupassisted C-H activation. The reaction generates C,C-palladacycles as the key intermediates that form two C(sp2)-C(sp3) bonds through reaction with CH2Br2. The reaction tolerates various functional groups, permitting easy access to a range of fluorene derivatives.
Pd-Catalyzed Assembly of Fluoren-9-ones by Merging of C-H Activation and Difluorocarbene Transfer
Liu, Xiaobing,Sheng, Heyun,Zhou, Yao,Song, Qiuling
supporting information, p. 2543 - 2547 (2021/05/05)
We disclose a novel Pd-catalyzed assembly of fluoren-9-ones by merging of C-H activation and difluorocarbene transfer. ClCF2COONa served as a difluorocarbene precursor to be harnessed as a carbonyl source in this transformation. The current protocol enables us to afford fluoren-9-ones in high yields with excellent functional group compatibility, which also represents the first example of using difluorocarbene as a coupling partner in transition-metal-catalyzed C-H activation.
Conversion of Aryl Aldehydes to Benzyl Iodides and Diarylmethanes by H3PO3/I2
Lv, Fang,Xiao, Jing,Xiang, Junchun,Guo, Fengzhe,Tang, Zi-Long,Han, Li-Biao
, p. 3081 - 3088 (2021/02/01)
For the first time, H3PO3 was used as both the reducing reagent and the promotor in the reductive benzylation reactions with aryl aldehydes. By using a H3PO3/I2 combination, various aromatic aldehydes underwent iodination reactions and Friedel-Crafts type reactions with arenes via benzyl iodide intermediates, readily producing benzyl iodides and diarylmethanes in good yields. Intramolecular cyclization reactions also took place, giving the corresponding cyclic compounds. This new strategy features easy-handling, low-cost, and metal-free conditions.
