N. E. Burlinson, S. Rettig, J. Trotter
May 1, 1986
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Journal
Canadian Journal of Chemistry
Abstract
A by-product formed in the preparation of tetrachloroguaiacol is shown to be a trimeric quinone. Derivatization of the quinone to a crystalline tetramethoxy derivative allowed X-ray determination of its crystal structure as 3,6-dichloro-4,5-dimethoxy-1,2-bis(2′-methoxy-3′,4′,5′,6′-tetrachlorophenoxy)benzene, 4. Rarely observed long range JCH coupling between ring carbons and methoxyl hydrogens as well as conformational isomerism were observed in 1H and 13C nmr studies of 4. Crystals of 4 are triclinic, a = 12.562 (1), b = 12.708(1), c = 9.223(1) A, α = 96.93(1), β = 97.478(7), γ = 101.285(8)°, Z = 2, space group. The structure was solved by direct methods and was refined by full-matrix least-squares procedures to R = 0.056 and Rw = 0.056 for 2946 reflections with I ≥ 1.5σ(I). The molecule contains a central six-membered dichloro-tetraoxo substituted aromatic ring, linked via oxygen bridges to two identical tetrachloro-dioxo substituted rings; intramolecular steric overcrowding causes significant deviation...