ScienceDirect - Tetrahedron Letters : Synthesis and properties of a novel cavity-forming ligand-system based on diphenylglycoluril

Tetrahedron Letters
Volume 27, Issue 2, 1986, Pages 243-246

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Diphenylglycoluril as a novel ligand architecture for d...
Inorganica Chimica Acta

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Diphenylglycoluril as a novel ligand architecture for dirhodium(II) carboxamidates
Inorganica Chimica Acta, Volume 361, Issue 11, 27 July 2008, Pages 3309-3314
Jason M. Nichols, Yu Liu, Peter Zavalij, Lyle Isaacs, Michael P. Doyle

Abstract

1,6-Bis-(N-benzyl)-diphenylglycoluril (1,6-BPGlyc) was used as a ligand in the synthesis of a dinuclear rhodium(II) paddlewheel complex. The ligand exchange reaction from Rh₂(OAc)₄ was remarkably selective for the formation of Rh₂(1,6-BPGlyc)₂(OAc)₂ with a cis-(1,3) ligand arrangement in 46% isolated yield. The bis-substitution pattern and diastereoselective ligand exchange is attributed to the steric bulk of the glycoluril backbone that prevents further ligand substitution. Rh₂(1,6-BPGlyc)₂(OAc)₂ catalyzes cyclopropanation reactions via decomposition of diazoacetates with reactivities and selectivities that were comparable to those of dirhodium(II) tetrakis-μ-carboxamidates.

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Prelim v-xiv contents (synopsis and pictogram)
Inorganica Chimica Acta

Prelim v-xiv contents (synopsis and pictogram)
Inorganica Chimica Acta, Volume 361, Issue 11, 27 July 2008, Pages iii-xiv

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doi:10.1016/S0040-4039(00)83987-8

Synthesis and properties of a novel cavity-forming ligand-system based on diphenylglycoluril

Frank G. M. Niele, Jan W. Zwikker and Roeland J. M. Nolte, ^*

Laboratory of Organic Chemistry, State University at Utrecht Padualaan 8, 3584 CH Utrecht, The Netherlands

Received 4 November 1985.

Available online 8 March 2001.

Abstract

The synthesis of a tetraimidazolyl ligand is described. Coordination to a metal centre affords a metallocryptand.

References

D.J. Cram and K.N. Trueblood Top. Curr. Chem. 98 (1981), p. 43. Full Text via CrossRef
R. Breslow Chem. Brit. (1983), p. 127.
J.M. Lehn Science 227 (1985), p. 849. View Record in Scopus | Cited By in Scopus (167)
I. Tabushi Tetrahedron 40 (1984), p. 269. Abstract | PDF (1472 K) | View Record in Scopus | Cited By in Scopus (33)

A.R. Butler and E. Leitch J. Chem. Soc. Perkin II 103 (1980).

All new compounds gave spectroscopic and analytical data consistent with their structures.

The glycerol matrix used for recording the FAB mass spectra contained sodium ions. During the measurement the transition metal ion can be reduced, c.f. R.L. Cerny, B.P. Sullivan, M.M. Bursey and T.J. Meyer Anal. Chem. 55 (1983), p. 1954. Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (3)

Conductivity measurements were performed in dry methanolic solutions (10⁻³ mol.dm⁻³) at 25°C. Under these conditions the conductivity of the Cl⁻ ion is 41 ohm⁻¹ cm² mol⁻¹; Cf. R.A. Robinson and R.M. Stokes In: Electrolyte Solutions, Butterworths, London (1959), p. 162.

A.W. Addison, K. Dawson, R.D. Gillard and H. Shaw J. Chem. Soc. Dalton (1972), p. 589. Full Text via CrossRef

Tetrahedron Letters
Volume 27, Issue 2, 1986, Pages 243-246

Result list | previous < 31 of 36 > next

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