Reactions of PO(NCS)3 with 4-Hydroxy-1,3-dioxanes. Crystal Structure of rel-(2S,4R,5S,6S)-2,6-Diethyl-5-methyl-4-(N'-benzylthioureido)-1,3-dioxane

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Title:Reactions of PO(NCS)3 with 4-Hydroxy-1,3-dioxanes. Crystal Structure of rel-(2S,4R,5S,6S)-2,6-Diethyl-5-methyl-4-(N'-benzylthioureido)-1,3-dioxane
Creators:
Bernát, Juraj
Kniežo, Ladislav
Birošová, Gabriela
Buděšínský, Miloš
Podlaha, Jaroslav
Podlahová, Jana
Novotný, Jiří
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 57, 6, pp. 1299-1313

Abstract

Substituted 4-hydroxy-1,3-dioxanes <i>II</i> react rapidly with PO(NCS)<sub>3</sub> to give 4-isothiocyanato-1,3-dioxanes <i>III</i>. The <sup>1</sup>H NMR spectra showed that in the isothiocyanate <i>IIIa</i> the predominant stereoisomer has its NCS group in axial position. The addition of benzylamine to the isothiocyanates <i>IIIa</i> and <i>IIIb</i> gave uniform thioureas <i>IVa</i> and <i>IVb</i> with equatorial alkyl groups at 2 and 6 positions and axial thioureido group at 4 position. On the other hand, the isothiocyanate <i>IIIc</i> reacts with benzylamine to give a mixture of three stereoisomeric thioureas <i>V,VI</i>, and <i>VIII</i>. The structure of <i>VI</i> was proved by means of X-ray diffraction analysis; in crystalline form the molecules of <i>VI</i> are present as H-bonded dimers (N-H<sup><strong>...</strong></sup>O).

Title:Reactions of PO(NCS)3 with 4-Hydroxy-1,3-dioxanes. Crystal Structure of rel-(2S,4R,5S,6S)-2,6-Diethyl-5-methyl-4-(N'-benzylthioureido)-1,3-dioxane
Creators:
Bernát, Juraj
Kniežo, Ladislav
Birošová, Gabriela
Buděšínský, Miloš
Podlaha, Jaroslav
Podlahová, Jana
Novotný, Jiří
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:57
Number:6
Page Range:pp. 1299-1313
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19921299UNSPECIFIED
ID Code:108
Item Type:Article
Deposited On:06 Feb 2009 16:39
Last Modified:06 Feb 2009 15:40

Citation

Bernát, Juraj; Kniežo, Ladislav; Birošová, Gabriela; Buděšínský, Miloš; Podlaha, Jaroslav; Podlahová, Jana; Novotný, Jiří (1992) Reactions of PO(NCS)3 with 4-Hydroxy-1,3-dioxanes. Crystal Structure of rel-(2S,4R,5S,6S)-2,6-Diethyl-5-methyl-4-(N'-benzylthioureido)-1,3-dioxane. Collection of Czechoslovak Chemical Communications, 57 (6). pp. 1299-1313. ISSN 0010-0765

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