- STEREOSPECIFIC CYCLISATIONS OF SUBSTITUTED α'-LITHIATED α(Z),γ-BUTADIENYL SULFOXIDES
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The title compounds 2(b-d) were prepared and converted stereospecifically to the lithiated derivatives of cyclic sulfoxides 3(b-d) through a proposed concerted disrotatory electrocyclisation.
- Reglier, Marius,Julia, Sylvestre A.
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- Synthesis and properties of substituted α'-lithiated α(Z),γ-butadienyl sulfoxides. Part I : Structural studies on sulfoxides obtained by stereospecific cyclisation of these compounds.
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The lithio-derivatives of sulfoxides 2b,c were prepared and gave stereospecifically after protonation the 2β-substituted 3,6-dihydro-4-methyl-2H-thiopyran-1α-oxides 3b,c.The latter were converted into the 1β-oxide 9b, the 2-substituted 3,6-dihydro-4-methyl-2H-thiopyrans 8b,c and the corresponding sulfones 10b,c.By comparison of the NMR spectra of these compounds as well as the effects of solvent (benzene) and europium salts on the chemical shifts of sulfoxides, the trans orientation of the sulfoxide group and R for 3b,c has been established.
- Reglier, M.,Julia, S. A.
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p. 226 - 235
(2007/10/02)
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