87792-25-4Relevant academic research and scientific papers
A (1)H Nuclear Magnetic Resonance Study of Alkyl- and Aryl-substituted 1,4-Oxathian-2-ones
Koskimies, Jorma K.
, p. 1449 - 1456 (2007/10/02)
(1)H N.m.r spectra for a number of alkyl- or aryl-substituted 1,4-oxathian-2-ones were analysed using the LAOCOON III program.The coupling constants imply that the C-S-C-C portion of the ring has a normal cyclohexane-like conformation which is compatible with either a classical boat or a half-chair.Chemical shift, geminal coupling constant, and long-range coupling constant evidence is presented which suggests that the former conformation is prevalent for oxathianones.Compounds with a single alkyl or phenyl substituent at C-3 or C-6 are conformationally biased, whereas the substituents at C-5 are mobile with ΔGo 1.0 and 1.7 kJ mol-1 for 5-methyl and 5-phenyl, respectively.
