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Structures of three disubstituted [13]-macrodilactones reveal effects of substitution on macrocycle conformation

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The synthesis and crystal structures of three new disubstituted [13]-macrodilactones, trans-4,8-dimethyl-1,10-dioxacyclotridec-5-ene-2,9-dione, cis-4-(4-bromophenyl)-13-methyl-1,10-dioxacyclotridec-5-ene-2,9-dione, and trans-11-methyl-4-phenyl-1,10-dioxacyclotridec-5-ene-2,9-dione are reported and their conformations are put in the context of other [13]-macrodilactone structures reported previously,… Click to show full abstract

The synthesis and crystal structures of three new disubstituted [13]-macrodilactones, trans-4,8-dimethyl-1,10-dioxacyclotridec-5-ene-2,9-dione, cis-4-(4-bromophenyl)-13-methyl-1,10-dioxacyclotridec-5-ene-2,9-dione, and trans-11-methyl-4-phenyl-1,10-dioxacyclotridec-5-ene-2,9-dione are reported and their conformations are put in the context of other [13]-macrodilactone structures reported previously, showing that the number, location, and relative disposition of groups attached at the termini of planar units of the [13]-macrodilactones subtly influence their aspect ratios.

Keywords: dioxacyclotridec ene; structures three; three disubstituted; disubstituted macrodilactones; ene dione; macrodilactones reveal

Journal Title: Acta Crystallographica Section E: Crystallographic Communications
Year Published: 2020

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