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(+/-)-6-Benzyl-3,3-dimethylmorpholine-2,5-dione and its 5-monothio and 2,5-dithio derivatives


Linden, Anthony; Pour, Fatemeh Ghorbani-Salman; Breitenmoser, Roland A; Heimgartner, Heinz (2001). (+/-)-6-Benzyl-3,3-dimethylmorpholine-2,5-dione and its 5-monothio and 2,5-dithio derivatives. Acta Crystallographica. Section C: Crystal Structure Communications, 57(5):634-637.

Abstract

The morpholine ring of the title dione, C13H15NO3, shows a boat conformation that is distorted towards a twist-boat, with the boat ends being the two Csp3 atoms of the ring. The benzyl substituent is in the favoured 'exo' position. In the monothione derivative, (+/-)-6-benzyl-3,3-dimethyl-5-thioxomorpholin-2-one, C13H15NO2S, this ring has a much flatter conformation that is midway between a boat and an envelope, with the dimethyl end being almost planar. The orientation of the benzyl group is 'endo'. The dithione derivative, (+/-)-6-benzyl-3,3-dimethylmorpholine-2,5-dithione, C13H15NOS2, has two symmetry-independent molecules, which show different puckering of the morpholine ring. One molecule has a flattened envelope conformation distorted towards a screw-boat, while the conformation in the other molecule is similar to that in the monothione derivative. Intermolecular hydrogen bonds link the molecules in the three compounds, respectively, into centrosymmetric dimers, infinite chains, and dimers made up of one of each of the symmetry-independent molecules.

Abstract

The morpholine ring of the title dione, C13H15NO3, shows a boat conformation that is distorted towards a twist-boat, with the boat ends being the two Csp3 atoms of the ring. The benzyl substituent is in the favoured 'exo' position. In the monothione derivative, (+/-)-6-benzyl-3,3-dimethyl-5-thioxomorpholin-2-one, C13H15NO2S, this ring has a much flatter conformation that is midway between a boat and an envelope, with the dimethyl end being almost planar. The orientation of the benzyl group is 'endo'. The dithione derivative, (+/-)-6-benzyl-3,3-dimethylmorpholine-2,5-dithione, C13H15NOS2, has two symmetry-independent molecules, which show different puckering of the morpholine ring. One molecule has a flattened envelope conformation distorted towards a screw-boat, while the conformation in the other molecule is similar to that in the monothione derivative. Intermolecular hydrogen bonds link the molecules in the three compounds, respectively, into centrosymmetric dimers, infinite chains, and dimers made up of one of each of the symmetry-independent molecules.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:2001
Deposited On:23 Oct 2013 06:29
Last Modified:05 Apr 2016 17:03
Publisher:Wiley-Blackwell
ISSN:0108-2701
Funders:Swiss National Science Foundation, F- Hoffmann-La Roche AG, Basel
Publisher DOI:https://doi.org/10.1107/S0108270101003195
PubMed ID:11353276

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