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Lithiation-methylation of thiasilinane 1-oxides

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Abstract

Lithiation-methylation of 3,3-dimethyl-1λ4,3-thiasilinane 1-oxide and 4,4-dimethyl-1λ4,4-thiasilinane 1-oxide under the action of butyllithium or lithium diisopropylamide and methyl iodide was studied. In both cases, monomethylation proceeds selectively α to the sulfoxide group to form 2,3,3-trimethyl-1λ4,3-thiasilinane 1-oxide and 2,4,4-trimethyl-1λ4,4-thiasilinane 1-oxide, respectively. Subsequently, 2,3,3-trimethyl-1λ4,3-thiasilinane 1-oxide undergoes monomethylation into the same α position to give 2,2,3,3-tetramethyl-1λ4,3-thiasilinane 1-oxide, while 4,4-dimethyl-1λ4,4-thiasilinane 1-oxide is dimethylated into the neighboring α’ position to form two stereoisomers of 2,4,4,6-tetramethyl-1λ4,4-thiasilinane 1-oxide with axial-equatorial or equatorial-equatorial methyl groups in the 2 and 6 positions.

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Authors and Affiliations

  1. Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, 664033, Irkutsk, Russia

    E. N. Suslova, A. I. Albanov & B. A. Shainyan

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  1. E. N. Suslova
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  2. A. I. Albanov
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  3. B. A. Shainyan
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Additional information

Original Russian Text © E.N. Suslova, A.I. Albanov, B.A. Shainyan, 2006, published in Zhurnal Obshchei Khimii, 2006, Vol. 76, No. 1, pp. 107–113.

For preliminary communication, see [1].

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Suslova, E.N., Albanov, A.I. & Shainyan, B.A. Lithiation-methylation of thiasilinane 1-oxides. Russ J Gen Chem 76, 103–109 (2006). https://doi.org/10.1134/S1070363206010191

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