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Synthesis of tricyclic ring systems: [2+2] ketene addition reaction for preparation of tricyclic ketone, alcohol, and lactone derivatives

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Abstract

The addition of dichloroketene to 1,4-cyclohexadiene was examined. Dichloroketene, which was easily prepared from trichloroacetyl chloride and Zn–Cu, reacted with 1,4-cyclohexadiene in the presence of POCl3 to afford novel racemic products of single addition (5) and double addition (6). The adducts 6 and 7 were reacted separately with MCPBA (meta-chloroperbenzoic acid), H2O2, LiAlH4, and cis-diol 10 was reacted with PCC (pyridinium chlorochromate) to afford lactone, alcohol, and ketone derivatives likely to exhibit biological activity. The structures of all the racemic molecules mentioned in the article were determined from 1H NMR, 13C NMR, MS, and IR data.

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Acknowledgement

The authors are indebted to Mersin University (BAP-FBE KA (ÖY) 2014-1DR, 2015-AP4-1235 and BAP-FBE K (EYB) 2011-7 YL) for its financial support of this work. The authors acknowledge Aksaray University, Science and Technology Application and Research Center, Aksaray, Turkey, for the use of the Bruker SMART BREEZE CCD diffractometer (purchased under grant No. 2010K120480 from the State Planning Organization).

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Arts and Sciences Mersin University, 33343, Mersin, Turkey

    Özgür Yılmaz, Esen Yıldız Bekfelavi & Nermin Şimşek Kuş

  2. Department of Science Education, Faculty of Education, Aksaray University, 68100, Aksaray, Turkey

    Tuncay Tunç

  3. Department of Chemistry, Faculty of Sciences Atatürk University, 25242, Erzurum, Turkey

    Ertan Şahin

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  1. Özgür Yılmaz
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  2. Esen Yıldız Bekfelavi
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Correspondence to Nermin Şimşek Kuş.

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Yılmaz, Ö., Bekfelavi, E.Y., Kuş, N.Ş. et al. Synthesis of tricyclic ring systems: [2+2] ketene addition reaction for preparation of tricyclic ketone, alcohol, and lactone derivatives. Chem. Pap. 71, 929–938 (2017). https://doi.org/10.1007/s11696-016-0013-7

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