Abstract
Iodonium ylides have recently attracted much attention on account of their synthetic applications. However, only a limited number of reports concerning the properties and reactivity of iodonium ylides exist, which is partly due to their instability. In this study, we synthesized several iodonium ylides that bear both an electron-withdrawing group and an aromatic ring with an ortho-t-BuSO2 group. Based on the crystal structures of the synthesized iodonium ylides in combination with natural-bond-orbital (NBO) calculations, we estimated the strength of the intra- and intermolecular halogen-bonding interactions. In addition, we investigated the reactivity of the iodonium ylides under photoirradiation.
Highlights
Iodonium ylides have for various synapplications, including condensations with thioamides to produce thiazole rings in aqueous thetic applications, including condensations with thioamides to produce thiazole rings in
The analysis demonstrated that the C14‒I1 σ* orbital of the expected, the distance between the iodine atom (I1) and the oxygen atom (O5) of the orthohypervalent iodine moiety in 2e overlaps with the three types of lone pairs (LPs) of the sulfonyl group in 2e (2.737(3) Å) is within the sum of the van der Waals radii, implying the intramolecular sulfonyl oxygen (O5)
We have synthesized a series of novel iodonium ylides that bear a coordinating ortho-tBuSO2 group on their aryl rings, and we have analyzed the crystal structures of two of these molecules
Summary
Iodoniumylides, ylides,aaclass classof ofhypervalent hypervalentiodine iodinecompounds compounds[1],. Iodonium ylides have beenbeen usedused for various synthetic reactions(Scheme (Scheme1a). Of particular to us are iodonium ylides that contain aortho coordinating group on the[8], aromatic [8], as ylides that contain a coordinating group on ortho the aromatic ring as suchring groups aresuch grou known to stabilize iodonium ylides and other hypervalent iodine compounds [5–9 known to stabilize iodonium ylides and other hypervalent iodine compounds [5,6,7,8,9], increasing their solubility via intramolecular halogen bonding (XB) In this stud increasing their solubility via intramolecular halogen bonding (XB) [10]. Investigated the reactivity ofthe these iodonium ylides under photoirradiation [24,25,26,27]
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