Nader Noroozi Pesyan - Department of Organic Chemistry, Faculty of Chemistry, Urmia University, ۵۷۱۵۹, Urmia, Iran
F. Karimi - Department of Organic Chemistry, Faculty of Chemistry, Urmia University, ۵۷۱۵۹, Urmia, Iran
H. Batmani - Department of Organic Chemistry, Faculty of Chemistry, Urmia University, ۵۷۱۵۹, Urmia, Iran
T. Tunç - Department of Science Education, Faculty of Education, Aksaray University, TR-۶۸۱۰۰, Aksaray, Turkey
E. Şahin - Department of Chemistry, Faculty of Science, Atatürk University, TR-۲۵۲۴۰ Erzurum, Turkey

Reaction of ۱,۳-cyclohexanedione, aldehydes, and cyanogen bromide leads to the selective formation of octahydro-۱H-xanthene-۱,۸(۲H)-diones in moderate to good yields at room temperature under basic condition. The reaction of dialdehydes such as phthalaldehyde and terphthalaldehyde gaves tetrahydrodibenzo[b,e]oxepin-۱(۲H)-one and bifunctiolalized linked bis-xanthen analogues, respectively. All structures were characterized by FT IR, ۱H and ۱۳C NMR spectroscopy and Mass analysis techniques. The structure of ۳c was analyzed by X-ray crystallography. The pKa and hydrogen bond strength (EHB) were determined in results of ≈۱۱.۷ and to ≈۵ kcal.mol-۱, respectively, via d(O•••••O) distance.

۱, ۳-cyclohexanedione, Octahydro-۱H-xanthene-۱, ۸(۲H)-dione, One-pot, Xanthene, Polymeric H-bond