Oxygen–oxygen cleavage in bicyclic trialkylperoxonium intermediates

Bloodworth, A. J.; Courtneidge, John L.; Eggelte, Henny J.

doi:10.1039/c39830001267

Cited by 8 publications

(11 citation statements)

References 2 publications

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“…Intermolecular H-bonds, however, are absent in the crystals of the two symmetrical ureines. high concentrations of the normal broadening effect of the 14N quadrupole on the NH resonances induced by the increase in the NH distance, which, in turn, results from intermolecular H-bonding (40,41). (iii) Remarkably high temperature coefficients of NH chemical shifts at high concentrations (42).…”

Section: Carbodiim Ides Nj"'dicyclohexy1carbodiimidementioning

confidence: 99%

“…data strongly support the view that the unsymmetrical ureines selfaggregate via N-H.*.O=C H-bonding in CDCl, more extensively than the symmetrical ureines do, in agreement with our findings in the crystal state described above. In DMSO, however, the sharpness (40,41) and chemical shifts of the NH resonances (to lower fields than the corresponding ones in CDCI,) (40) might be taken to imply that the ureines are effectively solvated via N-H.*.O=S Hbonding. In this strong H-bonding acceptor solvent (43) only small differences have been observed among the various ureines.…”

Section: Carbodiim Ides Nj"'dicyclohexy1carbodiimidementioning

confidence: 99%

“…The resonances of the NH protons of the two unsymmetrical ureines were unambiguously assigned on the basis of their different multiplicities. The most significant results are reported inTable 4.In CDCI, solution self-associa tion of ureines occurs to a high extent as indicated by: (i) The marked shift to lower fields of the NH resonances with increasing ureine concentration (39,40). (ii) The cancellation atFIGURE 4 Molecular and crystal structure of N,N'-diisopropylurea.…”

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confidence: 99%

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Methylene chloride‐soluble and insoluble ureines An X‐ray diffraction, infrared absorption, and proton magnetic resonance study

Toniolo

Valle

Bonora

et al. 1988

International Journal of Peptide and Protein Research

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An X‐ray diffraction study has been carried out on single crystals of two symmetrical ureines (N,N′‐diiopropylurea and the familiar N,N′‐dicyclohexylurea) and one unsymmetrical ureine (N‐tert.‐butyl.N′‐methylurea). The presence/absence of intermolecular H‐bonds in the crystal state has been compared to the situation assessed in solution by 1H n.m.r. It was shown by i.r. absorption that soluble ureines may disrupt intermolecular (peptide)N—H‐ O=C(peptide) H‐bonds in methylene chloride, a point of practical interest, particularly in solid‐phase peptide synthesis.

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Section: Carbodiim Ides Nj"'dicyclohexy1carbodiimidementioning

confidence: 99%

Section: Carbodiim Ides Nj"'dicyclohexy1carbodiimidementioning

confidence: 99%

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confidence: 99%

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Methylene chloride‐soluble and insoluble ureines An X‐ray diffraction, infrared absorption, and proton magnetic resonance study

Toniolo

Valle

Bonora

et al. 1988

International Journal of Peptide and Protein Research

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“…Several reports indicate that the halogenation of organomercurials prepared by solvomercuration reactions provides a convenient method for the synthesis of P-substituted organic halides [eq. The iodination of (45) alken~l-[*~I, alkynyl-[90, 911 and arylmer~urials~~~] also appears to be of preparative utility. (45)] [88].…”

Section: Halogenation Of Organomercury Compoundsmentioning

confidence: 99%

“…(45)] [88]. The iodination of (45) alken~l-[*~I, alkynyl-[90, 911 and arylmer~urials~~~] also appears to be of preparative utility.…”

Section: Halogenation Of Organomercury Compoundsmentioning

confidence: 99%

Organomercury Compounds in Organic Synthesis

Larock

1985

Reactivity and Structure Concepts in Organic Chemistry

101

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Organomercurials have been known since 1850 and many synthetic routes to these compounds presently exist. The ability of these compounds to accommodate a wide variety of functional groups and to tolerate quite diverse reaction conditions makes them attractive as synthetic intermediates. While the ~~lv~mercuration-demercuration and divalent carbon transfer reactions remain the most widely used of the organomercurial reactions, a number of new synthetic procedures employing organomercurials have been developed in recent years. Many of these involve transmetallation reactions with palladium salts.

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