Studies on the intramolecular C[bond]H...X (X = O, S) interactions in (S)-N-acyl- 4-isopropyl-1,3-thiazolidine-2-thiones and related 1,3-oxazolidin-2-ones

Anabel Cosp; Igor Larrosa; Josep M Anglada; Josep M Bofill; Pedro Romea; Fèlix Urpí

doi:10.1021/ol0347848

Studies on the intramolecular C[bond]H...X (X = O, S) interactions in (S)-N-acyl- 4-isopropyl-1,3-thiazolidine-2-thiones and related 1,3-oxazolidin-2-ones

Org Lett. 2003 Aug 7;5(16):2809-12. doi: 10.1021/ol0347848.

Authors

Anabel Cosp¹, Igor Larrosa, Josep M Anglada, Josep M Bofill, Pedro Romea, Fèlix Urpí

Affiliation

¹ Departament de Química Orgànica, Universitat de Barcelona, Martí i Franqués 1-11, 08028 Barcelona, Catalonia, Spain.

PMID: 12889880
DOI: 10.1021/ol0347848

Abstract

[reaction: see text] Two intramolecular C[bond]H...X (X = O, S) interactions in (S)-N-acyl-4-isopropyl-1,3-thiazolidine-2-thiones are documented through crystallographic and spectroscopic evidence and high-level theoretical calculations. The key role played by the sulfur atoms has been made clear by comparison with structurally related (S)-N-acyl-4-isopropyl-1,3-oxazolidin-2-ones.