4-Thio derivatives of sydnone imines

Cherepanov, I. A.; Lebedev, S. N.; Samarskaya, Alina S.; Godovikov, Ivan A.; Nelyubina, Yulia V.; Калинин, В. Н.

doi:10.1016/j.mencom.2009.11.009

Cited by 18 publications

(13 citation statements)

References 6 publications

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“…1 4 ) along them. We found an example in CUGBIQ (Cherepanov et al, 2009) suggesting an a$b swapping. Finally, the matrix transformation (0 1 0, 1 0 0, 0 À 1 2 1 2 ) leads to a pseudo-monoclinic cell with V 0 = 1 2 V, and to a clear P2 1 /n disposition of the symmetry elements [transformed data: a = 11.2447 (4), b = 10.2520 (4), c = 14.3198 (6) Å , = 90.916 (5), = 125.709 (4) and = 90.574 (5) ; see Fig.…”

Section: Figurementioning

confidence: 77%

“…parallel to [100], [110] and [110], but no trace of any [010] one can be found, as would be expected for a pseudo-tetragonal pseudosymmetry, thus confirming this to be a case where metrics and structure do not correlate. Cherepanov et al, 2009; full details are available in file SM2c in the supporting information). On occasions, it is not just the disposition of the pseudo-axis which suggests a unit-cell transformation, but instead the existence of some particular directions with cell halving and/or fractional shifts (e.g.…”

Section: Figurementioning

confidence: 99%

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A simple graphical method to pinpoint local pseudosymmetries inZ′ > 1 cases

Baggio

2019

Acta Crystallogr C Struct Chem

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An intuitive method is presented for detecting pseudosymmetries in Z′ > 1 cases as a complement to well‐proven strategies already available in the literature. It is based in the simple idea that the mid‐points between equivalent atoms in symmetrically related molecules are disposed according to simple well‐known patterns, which are easily recognizable by optical inspection. A number of Z′ = 4 cases in the literature are analyzed, which allows some of the potentialities of the method to be revealed.

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Section: Figurementioning

confidence: 77%

Section: Figurementioning

confidence: 99%

A simple graphical method to pinpoint local pseudosymmetries inZ′ > 1 cases

Baggio

2019

Acta Crystallogr C Struct Chem

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“…indicates a covalent bond character between t BuLi and n BuLi for the Li–C bond of the carbene 8c . Sydnone imine anions form gold and palladium complexes and undergo reactions with S and Se . To the best of our knowledge, however, trapping reactions with CO 2 , isocyanates and isothiocyanates have not yet been described.…”

Section: Resultsmentioning

confidence: 99%

Heterocycle Syntheses with Anionic N‐Heterocyclic Carbenes: Ring Transformations of Sydnone Imine Anions

et al. 2018

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Sydnone imines were deprotonated at the C4 position to give lithium‐stabilized anions, which proved to be stable for several months in solution. These anions are elements of the intersection of the substance classes of N‐heterocyclic carbenes and mesomeric betaines. They can be formulated as anionic N‐heterocyclic carbenes. The negative charge translates into high‐field shifts of the 13C NMR resonance frequencies of C4 in comparison to other NHCs. Similar to the chemistry of N‐heterocyclic carbenes, reactions with isocyanates and isothiocyanates gave 4‐(N‐carbamoyl)‐benzoylsydnone imines in trapping reactions. As a result of ring transformations involving the characteristic π‐architecture of the mesoionic framework, imidazolidine‐2,4‐dithiones, imidazolin‐2,4‐diones and 1,2,4‐triazol‐5‐ones were formed depending on the substitution pattern of the starting materials and the reaction conditions.

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“…Thiols of sydnone imines are very rare. 21 Methylation by modied literature procedures yielded the stable 21,22 sydnone imine thioethers 25a,b in acceptable yields. We were able to oxidize the thioethers 25a,b with m-chloroperoxybenzoic acid to give the sulfoxides 26a,b.…”

Section: Resultsmentioning

confidence: 99%