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(±)-6-Benzyl-3,3-di­methyl­morpholine-2,5-dione and its 5-mono­thio and 2,5-di­thio derivatives by Anthony Linden; Fatemeh Ghorbani-Salman Pour; Roland A. Breitenmoser; Heinz Heimgartner is a Chemistry article available to read on EtoBox.

What is (±)-6-Benzyl-3,3-di­methyl­morpholine-2,5-dione and its 5-mono­thio and 2,5-di­thio derivatives about?

The morpholine ring of the title dione, C(13)H(15)NO(3), shows a boat conformation that is distorted towards a twist-boat, with the boat ends being the two Csp(3) 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, C(13)H(15)NO(2)S, 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, C(13)H(15)NOS(2), 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.

Who reads (±)-6-Benzyl-3,3-di­methyl­morpholine-2,5-dione and its 5-mono­thio and 2,5-di­thio derivatives?

Author

Anthony Linden; Fatemeh Ghorbani-Salman Pour; Roland A. Breitenmoser; Heinz Heimgartner

Publisher

International Union of Crystallography; Blackwell Publishing Inc.; International Union of Crystallography (IUCr); Wiley (ISSN 0108-2701)

Published

2001

Language

EN

Field

Chemistry (Physical Sciences)