Stereodynamics of 1-(methylsulfonyl)-3,5-bis(trifluoromethylsulfonyl)-1,3,5-triazinane: experimental and theoretical analysis

Bagrat A Shainyan; Igor A Ushakov; Andreas Koch; Erich Kleinpeter

doi:10.1021/jo061112x

Stereodynamics of 1-(methylsulfonyl)-3,5-bis(trifluoromethylsulfonyl)-1,3,5-triazinane: experimental and theoretical analysis

J Org Chem. 2006 Sep 29;71(20):7638-42. doi: 10.1021/jo061112x.

Authors

Bagrat A Shainyan¹, Igor A Ushakov, Andreas Koch, Erich Kleinpeter

Affiliation

¹ Irkutsk Institute of Chemistry, Siberian Division of Russian Academy of Sciences, Irkutsk, Russia. bagrat@irioch.irk.ru

PMID: 16995668
DOI: 10.1021/jo061112x

Abstract

Dynamic NMR of 1-(methylsulfonyl)-3,5-bis(trifluoromethylsulfonyl)-1,3,5-triazinane reveals the existence of three conformers and two dynamic processes: ring inversion and rotation about the N-S bond, both processes having DeltaG(++) = 13.5 kcal/mol. An unprecedented large reverse Perlin effect (J(CHax) > J(CHeq)) was found experimentally and calculated theoretically.