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Issue 11, 2013
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Synthesis and structural studies on thioimides, R2C[double bond, length as m-dash]NSR and sulfur diimides, R2C[double bond, length as m-dash]NSN[double bond, length as m-dash]CR2

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Abstract

Reaction of Ph2C[double bond, length as m-dash]O and py2C[double bond, length as m-dash]O with Li[N(SiMe3)2] and ArSCl (Ar = 2-O2NC6H4, 2,4-(O2N)2C6H3) yielded Ph2C[double bond, length as m-dash]NSAr (1a and 1b respectively) and py2C[double bond, length as m-dash]NSAr (2a and 2b respectively). Reaction of fluorenone, C12H8C[double bond, length as m-dash]O 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 py2C[double bond, length as m-dash]O 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.

Graphical abstract: Synthesis and structural studies on thioimides, R2C [[double bond, length as m-dash]] NSR and sulfur diimides, R2C [[double bond, length as m-dash]] NSN [[double bond, length as m-dash]] CR2

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Publication details

The article was received on 01 Dec 2012, accepted on 26 Dec 2012, published on 04 Jan 2013 and first published online on 04 Jan 2013


Article type: Paper
DOI: 10.1039/C2DT32878J
Citation: Dalton Trans., 2013,42, 3888-3895
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    Synthesis and structural studies on thioimides, R2C[double bond, length as m-dash]NSR and sulfur diimides, R2C[double bond, length as m-dash]NSN[double bond, length as m-dash]CR2

    R. L. Melen, D. J. Eisler, R. A. Hewitt and J. M. Rawson, Dalton Trans., 2013, 42, 3888
    DOI: 10.1039/C2DT32878J

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