Conclusions
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1.
The introduction of a condensed benzene ring into a macrocyclic ansa system that includes the thiophene nucleus sharply lowers the conformational mobility of the molecule.
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2.
The NMR spectroscopy data show that conformations are realized for 2,3-benzo-5-oxa-[10]-α-1,4-cyclothienedione (III) and [10]-α-1-cyclothienone (II) in solution that are close to the conformation established for the crystalline state.
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Literature cited
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Additional information
N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow. Translated from Izvestiya Akademii Nauk SSSR Seriya Khimicheskaya, No. 10, pp. 2343–2346, October, 1976.
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Alashev, F.D., Taits, Z.S. & Gol'dfarb, Y.L. NMR spectra and conformation of a macrocyclic ketolactone, 2,3-benzo-5-oxa-[10]-α-1,4-cyclothienedione. Russ Chem Bull 25, 2187–2189 (1976). https://doi.org/10.1007/BF02659545
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DOI: https://doi.org/10.1007/BF02659545