Conformational analysis 29: Preparation and1H and13C NMR, FTIR, MS, and crystallographic conformational and configurational study of 3-Oxo-1,3-oxathiane and its monomethyl ... View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

1993-06

AUTHORS

Kalevi Pihlaja, Reijo Sillanpää, Martti Dahlqvist, Géza Stájer, Markku Ahlgren

ABSTRACT

3-Oxo-1,3-oxathiane (1) and its monomethyl derivatives were prepared by oxidation of the corresponding 1,3-oxathianes. The structural analysis was carried out by1H and13C NMR, FTIR, and mass spectrometry. At 298 K compound1 was a 1 ∶ 1 (at 173 K a 3 ∶ 1) mixture of the SO(ax) and SO(eq) chair forms. The major oxidation products of methyl 1,3-oxathianes attained exclusively the SO(ax), Me(eq) chair forms except that of the 5-methyl derivative, which consisted of 7% of the SO(eq), Me(ax) chair conformation in CDCl3 solution. The minor products of oxidation existed in anancomeric SO(eq), Me(eq) chair conformations. The oxidation of 2-methyl- 1,3-oxathiane, however, led to 3,3-dioxo derivative (6) in addition to thetrans [SO(eq)] monoxide. The crystal structures of6 andtrans-3-oxo-5-methyl-1,3-oxathiane were solved by X-ray diffractometry. More... »

PAGES

203-210

Identifiers

URI

http://scigraph.springernature.com/pub.10.1007/bf00679347

DOI

http://dx.doi.org/10.1007/bf00679347

DIMENSIONS

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