ChemInform Abstract: A REMARKABLE DIFFERENCE IN THE CONFORMATIONAL PREFERENCE OF THE SO‐BOND IN 1,3‐DITHIANE‐1‐OXIDES AND 1,3‐OXATHIANE‐3‐OXIDES

2-Aryl-5-tert-butyl-1,3-dithianes and their S-oxidation products: structure-activity relationships of potent insecticides acting at the GABA-gated chloride channel

“…Monosulfoxides. In agreement with the established conformational preference of the S=0 bond in 1,3-dithiane sulfoxides (Carey et al, 1974;Tonge, 1973,1974;Juaristietal., 1984;Van Acker and Anteunis, 1974), monosulfoxide C formed from MCPBA oxidation of A has the S=0 bond equatorial. The stereochemistry of each monosulfoxide from A is assigned on the basis of the NMR chemical shift of C-5 (Carey et al, 1978) and the IR stretching frequency of the sulfoxide bond (i>SO) (Otting and Neugebauer, 1962) (Table IV).…”

1H and 13C NMR Spectral Study of Some 2r-Aryl-6c-phenylthian-4-ones, Their 1-Oxides and 1,1-Dioxides

“…[16] However, replacement of a methylene group at the b-position by a heteroatom or the replacement of a b-axial hydrogen by a methyl group increases the population of the S¼O equatorial conformation. [17,18] The replacement of a-methylene group by sulfur results in a greater predominance of the S¼O axial conformation. [19À21] In the current case, the S¼O equatorial conformation 2C 0 will have the phenyl and aryl groups in the axial positions.…”