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An improved synthesis and structural characterisation of 2-(4-acetylthiophenylethynyl)-4-nitro-5-phenylethynylaniline: The molecule showing high negative differential resistance (NDR)

Wang, C.S.; Batsanov, A.S.; Bryce, M.R.; Sage, I.

Authors

C.S. Wang

A.S. Batsanov

I. Sage



Abstract

2-(4-Acetylthiophenylethynyl)-4-nitro-5-phenyl-ethynylaniline (11) has been synthesised by an improved route, which has many advantages over the literature procedure. A key intermediate is 2-ethynyl-4-nitro-5-phenylethynylaniline (6) which is obtained from 2,5-dibromoacetanilide (5 steps, 68% overall yield). Reaction of 6 with 1-acetylthio-4-iodobenzene under Sonogashira coupling conditions affords 11 (56%). Compound 11 is characterised by CHN analysis, mass spectrometry and H-1 and C-13 NMR spectroscopy. The crystal structures of 2-bromo-4-nitro-5-phenylethynylaniline line (4), 2-(3-hydroxy-3-methylbutynyl)-4-nitro-5-phenylethynylaniline (5) and 2-[(4-methoxybenzylthio)phenylethynyl] -4-nitro-5-phenylethynylaniline (15), have been determined, by which the regiochemical structure of 11 is also proved. The intramolecular contacts O(1)...C(7) of 2.692(2) Angstrom in 4 and 2.677(2) Angstrom in 15 are considerably shorter than the standard van der Waals O...C contact of 3.24 Angstrom.

Citation

Wang, C., Batsanov, A., Bryce, M., & Sage, I. (2003). An improved synthesis and structural characterisation of 2-(4-acetylthiophenylethynyl)-4-nitro-5-phenylethynylaniline: The molecule showing high negative differential resistance (NDR). Synthesis: Journal of Synthetic Organic Chemistry, 2089-2095

Journal Article Type Article
Publication Date 2003-09
Journal Synthesis : journal of synthetic organic chemistry.
Print ISSN 0039-7881
Publisher Thieme Gruppe
Peer Reviewed Peer Reviewed
Issue 13
Pages 2089-2095