Synthesis of 5-(2-methoxy-1-naphthyl)- and 5-[2-(methoxymethyl)-1-naphthyl]-11H-benzo[b]fluorene as 2,2'-disubstituted 1,1'-binaphthyls via benzannulated enyne–allenes

Yu-Hsuan Wang, Joshua F. Bailey, Jeffrey L. Petersen and Kung K. Wang
Beilstein J. Org. Chem. 2011, 7, 496–502. https://doi.org/10.3762/bjoc.7.58

Supporting Information

Supporting Information File 1: Experimental procedures, spectroscopic data, and 1H and/or 13C NMR spectra of 5a,b, 6a,b, 8a,b, 9a,b, 13a,b, 17, 18b, 19ac, 20ac, 2124, and the (1S)-camphanates of 24.
Format: PDF Size: 5.6 MB Download

Cite the Following Article

Synthesis of 5-(2-methoxy-1-naphthyl)- and 5-[2-(methoxymethyl)-1-naphthyl]-11H-benzo[b]fluorene as 2,2'-disubstituted 1,1'-binaphthyls via benzannulated enyne–allenes
Yu-Hsuan Wang, Joshua F. Bailey, Jeffrey L. Petersen and Kung K. Wang
Beilstein J. Org. Chem. 2011, 7, 496–502. https://doi.org/10.3762/bjoc.7.58

How to Cite

Wang, Y.-H.; Bailey, J. F.; Petersen, J. L.; Wang, K. K. Beilstein J. Org. Chem. 2011, 7, 496–502. doi:10.3762/bjoc.7.58

Download Citation

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.

Citations to This Article

Up to 20 of the most recent references are displayed here.

Scholarly Works

  • Wu, X.; Xue, L.; Li, D.; Jia, S.; Ao, J.; Deng, J.; Yan, H. Organocatalytic Intramolecular [4+2] Cycloaddition between In Situ Generated Vinylidene ortho‐Quinone Methides and Benzofurans. Angewandte Chemie 2017, 129, 13910–13914. doi:10.1002/ange.201707523
  • Wu, X.; Xue, L.; Li, D.; Jia, S.; Ao, J.; Deng, J.; Yan, H. Organocatalytic Intramolecular [4+2] Cycloaddition between In Situ Generated Vinylidene ortho-Quinone Methides and Benzofurans. Angewandte Chemie (International ed. in English) 2017, 56, 13722–13726. doi:10.1002/anie.201707523
  • Rana, A.; Paul, I.; Schmittel, M. Dynamic effects in the didehydro-Diels-Alder (DDDA) reaction of enyne-ketoenes: 50% stepwise bond formation in spite of concerted transition state†. Journal of Physical Organic Chemistry 2017, 30. doi:10.1002/poc.3732
  • Sun, N.; Xie, X.; Wang, G.; Chen, H.; Liu, Y. Base‐Catalyzed Cyclization of 1,6‐Diynyl Carboxylates Involving Propargyl‐Allenyl Isomerization: Efficient Synthesis of Benzo[b]fluorene and Its Analogues. Advanced Synthesis & Catalysis 2017, 359, 1394–1401. doi:10.1002/adsc.201601074
  • Raviola, C.; Protti, S.; Ravelli, D.; Fagnoni, M. (Hetero)aromatics from dienynes, enediynes and enyne-allenes. Chemical Society reviews 2016, 45, 4364–4390. doi:10.1039/c6cs00128a
  • Roy, J.; Mal, T.; Jana, S.; Mal, D. Regiodefined synthesis of brominated hydroxyanthraquinones related to proisocrinins. Beilstein journal of organic chemistry 2016, 12, 531–536. doi:10.3762/bjoc.12.52
  • Rana, A.; Cinar, M. E.; Samanta, D.; Schmittel, M. Solving the puzzling competition of the thermal C2–C6 vs Myers–Saito cyclization of enyne-carbodiimides. Beilstein journal of organic chemistry 2016, 12, 43–49. doi:10.3762/bjoc.12.6
  • Manojveer, S.; Balamurugan, R. A facile access to substituted benzo[a]fluorenes from o-alkynylbenzaldehydes via in situ formed acetals. Chemical communications (Cambridge, England) 2014, 50, 9925–9928. doi:10.1039/c4cc03934c
  • doi:10.1002/9781118709313.refs
  • Allen, A. D.; Tidwell, T. T. Ketenes and Other Cumulenes as Reactive Intermediates. Chemical reviews 2013, 113, 7287–7342. doi:10.1021/cr3005263
  • Schmittel, M.; Vavilala, C.; Cinar, M. E. The thermal C2–C6 (Schmittel)/ene cyclization of enyne–allenes – crossing the boundary between classical and nonstatistical kinetics. Journal of Physical Organic Chemistry 2011, 25, 182–197. doi:10.1002/poc.1887
Other Beilstein-Institut Open Science Activities