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Synthesis and structure of 2-aryl-5,5-disubstituted-1,3-dioxanes and conversion into chiral (1,1,1-trishydroxymethyl) methane derivatives

✍ Scribed by John M Gardiner; Paul Mather; Ramy Morjan; Robin G Pritchard; John E Warren; Malcolm L Cooper; Abd El-Rahman S Ferwanah; Omar S Abu-Tiem

Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
173 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis

Pentaerythritol, (1,1,1-trishydroxymethyl)methyl methane and (1,1,1-trishydroxymethyl)nitromethane are converted into 2-aryl-5,5-bis(hydroxymethyl), 2-aryl-5-hydroxymethyl-5-methyl-or 2-aryl-5-hydroxymethyl-5-nitro-1,3-dioxanes and a range of derivatives. X-Ray and NMR analysis establishes that the latter is obtained as a single diastereomer whose structure is unambiguously determined. These materials can be elaborated to chiral derivatives of the starting (1,1,1-trishydroxymethyl) methanes.

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