X-ray structural investigation of the products of ring closure of 2-alkenylthiopyridines upon treatment with mercury iodide

A single crystal X-ray study of the products of halogen mercury cyclization of 8-allylthioquinoline

“…Thus, the lengths of the С-Нg bond ( Table 2) are well consistent with a tabular value of 2.07(1) Å [10], although they are slightly smaller than those found in [4] for the products of mercury cyclization of 2-alkenylthiopyridines 5; С-Нg-X bond angles are close to 180°; the lengths of the С-C bonds of the heterocycle do not exhibit any deviation from the norm either. Nitrogen and mercury atoms are in the gauche conformation relative to the axis of the C(11)-C(12) bond; hence, sulfur and mercury atoms are spatially proximate (d(Нg…S) = 3.17-3.21 Å, Table 2).…”

“…Our study has shown that the reaction of 8-allylthioquinoline 1 with HgХ 2 (Х = Cl, Br, I) leads to the formation of derivatives of 2,3-dihydro [1,4] 3-(Bromomercurimethyl)-2,3-dihydro [1,4]thiazino[2,3,4-ij] quinolinium tetrabromomercurate 2b according to the single crystal XRD data. crystallographically independent structural units of the HetHgX + cation; the counterion is the doubly charged 2 4 HgX − anion.…”

“…Previously, it was shown [3,4] that mercury halides react with 2-allylthiopyridine and its derivatives to form organomercury salts of 2,3-dihydrothiazolo[3,2-a]pyridinium. The purpose of this paper is single crystal X-ray studies of the reaction products of HgX 2 (Х = Сl, Br, I) with 8-allylthioquinoline (1) (products 2a-c) and 8-ethylthioquinoline (3) (product 4).…”

“…EXPERIMENTAL 8-Allylthioquinoline and 8-ethylthioquinoline were obtained by the procedure described in [5,6]. Preparation of 3-(halogenomercurimethyl)-2,3-dihydro [1,4]thiazino [2,3,4-ij]quinolinium halogenomercurates (general procedure). A solution of 1.2 mmol mercury(II) halide in 10 ml of solvent is added to a solution of 0.24 g (1.2 mmol) of 8-allylthioquinoline in 10 ml of acetone or EtOH.…”

“…3-(Chloromercurimethyl)-2,3-dihydro [1,4] an Xcalibur 3 automated four-circle diffractometer with a CCD detector. The measurement temperature was 295(2) K; the radiation wavelength was 0.71073 Å (MoK α ).…”