ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

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

Özgür Yılmaz, Esen Yıldız Bekfelavi, Nermin Şimşek Kuş, Tuncay Tunç, and Ertan Şahin

Department of Chemistry, Faculty of Arts and Sciences Mersin University, Mersin, Turkey

E-mail: simner@mersin.edu.tr

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.

Keywords: Ketene addition; Tricyclic molecules; Lactone; Ketone

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-016-0013-7

Chemical Papers 71 (5) 929–938 (2017)