Issue 6, 2017

S-Functionalization of 3,5-bis(2-pyridyl)-1,2,4,6-thiatriazine: probing the effect of alkyl chain length in the development of tethered materials

Abstract

Reactions between 3,5-bis(2-pyridyl)-4-hydro-1,2,4,6-thiatriazine (Py2TTAH) and a series of 1,n-dibromoalkanes (n = 2, 3, 4, 5, 6, 8, 10) were explored and a synthetic route to prepare tethered 3,5-bis-(2-pyridyl)-1λ4,2,4,6-thiatriazines is described. When the length of the alkyl group employed is n ≥ 4, S,S′-alkyl-bis(Py2TTA) derivatives (8–12) are isolated; however, if n < 4, S-cyclopropyl-Py2TTA (13; n = 3) and S-ethenyl-Py2TTA (14; n = 2) are formed due to competitive intramolecular SN2 cyclization and E2 reactions, respectively. NMR spectroscopy, electron spray ionization mass spectrometry and X-ray crystallography were used to probe the dependence of the alkyl chain length on the reaction pathway. Computational studies are also presented, which support the preference of intramolecular vs. intermolecular SN2 reactions when n = 3 and n > 3, respectively.

Graphical abstract: S-Functionalization of 3,5-bis(2-pyridyl)-1,2,4,6-thiatriazine: probing the effect of alkyl chain length in the development of tethered materials

Supplementary files

Article information

Article type
Paper
Submitted
29 Nov 2016
Accepted
06 Feb 2017
First published
16 Feb 2017

New J. Chem., 2017,41, 2268-2276

S-Functionalization of 3,5-bis(2-pyridyl)-1,2,4,6-thiatriazine: probing the effect of alkyl chain length in the development of tethered materials

N. J. Yutronkie, P. Tami, S. Singh, E. Kleisath, B. M. Gabidullin, R. Davis and J. L. Brusso, New J. Chem., 2017, 41, 2268 DOI: 10.1039/C6NJ03721F

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