Synthesis and structural studies on thioimides, R2CNSR and sulfur diimides, R2CNSNCR2

Melen, Rebecca L. ORCID: https://orcid.org/0000-0003-3142-2831, Eisler, Dana J., Hewitt, Rachel A. and Rawson, Jeremy M. 2013. Synthesis and structural studies on thioimides, R2CNSR and sulfur diimides, R2CNSNCR2. Dalton Transactions 42 (11) , pp. 3888-3895. 10.1039/c2dt32878j

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Abstract

Reaction of Ph2CO and py2CO with Li[N(SiMe3)2] and ArSCl (Ar = 2-O2NC6H4, 2,4-(O2N)2C6H3) yielded Ph2CNSAr (1a and 1b respectively) and py2CNSAr (2a and 2b respectively). Reaction of fluorenone, C12H8CO with Li[N(SiMe3)2] and ArSCl under similar conditions afforded C12H8CNSAr (3a and 3b respectively). Whilst reaction of fluorenone with Li[N(SiMe3)2] and SCl2 in a 2:2:1 ratio afforded the sulfur-diimide, C12H8CNSNCC12H8 (4), reaction of py2CO with Li[N(SiMe3)2] and SCl2 under similar conditions afforded the thiazyl heterocycle [py2CNS]Cl (5) via intramolecular coordination. The structures of 1a, 1b, 2a, 2b, 3a, 3b and 4 are determined by X-ray diffraction. In the case of 4, bond lengths and DFT studies reveal greater π-delocalisation than in 1–3.

Item Type:	Article
Status:	Published
Schools:	Chemistry
Subjects:	Q Science > QD Chemistry
Publisher:	Royal Society of Chemistry
ISSN:	1477-9226
Date of Acceptance:	26 December 2012
Last Modified:	27 Oct 2022 09:16
URI:	https://orca.cardiff.ac.uk/id/eprint/65044

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