P. Jones, G. Sheldrick, A. Kirby
Oct 1, 1982
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Influential Citations
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Journal
Zeitschrift für Kristallographie - Crystalline Materials
Abstract
The crystal structure of the title compound has been determined (space group Ρ J, a = 6.774(3), b = 8.900(4), c = 9.811(4) Α, α = 66.06(2), /3 = 86.67(3), y = 76.87(2)°, Ζ = 2) and refined to R = 0.040. The bond lengths at the acetal centre are consistent with a previously published bond· length/reactivity correlation (Jones and Kirby, 1979). Introduction We have shown recently (Jones and Kirby, 1979) that there is a linear correlation between reactivity and the length of the exocyclic C — Ο bond in a series of three 2-aryloxy-tetrahydropyran acetals. To test the strength of this correlation we have prepared several more acetals in this series, and report here the crystal and molecular structure of one of the simplest such compounds to exist in crystalline form at room temperature, the 4-chlorophenoxy acetal (1). (1) was prepared by the acid-catalysed addition of p-chlorophenol to dihydropyran. The phenol (0.025 mol) and dihydropyran (0.05 mol) were dissolved in dry ether and a few crystals of p-toluenesulphonic acid added. After stirring for 3 h under nitrogen, the solution was allowed to stand 1 Crystal Structures of Acetals, Part 6. Parts 1—5 are the first five references 2 All correspondence to P.G.J, (above address) 266 P. G. Jones et al.: The crystal structure of 2-(4'-chlorophenoxy)-tetrahydropyrran Table 1. Atom coordinates ( χ 10) and temperature factors (Α χ 10 ). The anisotropic termperature factor has the form 7~= — 2π {£/,, h a* + . . . 2 Vi2 hka*b* + ... J