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

Melen, Rebecca L., 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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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: 04 Jun 2017 06:49

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