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3 article(s) from Kollenz, Gert

From dipivaloylketene to tetraoxaadamantanes

Gert Kollenz and
Curt Wentrup

Beilstein J. Org. Chem. 2018, 14, 1–10, doi:10.3762/bjoc.14.1

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Graphical Abstract

Scheme 1: Synthetic routes to 2,4,6,8-tetraoxaadamantanes.

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Scheme 2: Conversion of dipivaloylketene (2) to bisdioxines (2,6,9-trioxabicyclo[3.3.1]nona-3,7-dienes) 4 and...

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Scheme 3: 2,6,9-Trioxabicyclo[3.3.1]nonadienes (bisdioxines, 9–13) derived from dipivaloylketene (2).

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Scheme 4: Mechanisms of formation of bisdioxine acid derivatives from dimer 3.

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Scheme 5: Recently reported synthesis of chromenobisdioxines.

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Scheme 6: Formation of tetraoxaadamantanes.

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Scheme 7: Decarboxylative hydrolysis and oxa-Michael-type ring closure.

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Scheme 8: Oxime and hydrazine derivatives of bisdioxines and tetraoxaadamantanes.

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Figure 1: Bistetraoxaadamantane derivatives.

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Scheme 9: Inward-pointing isocyanate, urethane and carbamate groups in bisdioxines. The diisocyanate is obtai...

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Scheme 10: Microwave-assisted tetraoxaadamantane formation.

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Scheme 11: Cyclic bisdioxine ester derivative 34 forming a single mono-tetraoxaadamantane.

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Figure 2: Cyclic bisdioxine derivative not forming a tetraoxaadamantane due to reduced cavity size.

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Figure 3: The bisdioxine-calix[6]arene derivative 37 complexes Cs⁺ but does not form a tetraoxaadamantane der...

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Review

Published 02 Jan 2018

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Molecular cleft or tweezer compounds derived from trioxabicyclo[3.3.1]nonadiene diisocyanate and diacid dichloride

Gert Kollenz,
Ralf Smounig,
Ferdinand Belaj,
David Kvaskoff and
Curt Wentrup

Beilstein J. Org. Chem. 2015, 11, 1–8, doi:10.3762/bjoc.11.1

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Figure 1: 2,6,9-Trioxabicyclo[3.3.1]nonadiene (“bisdioxine”) derivatives.

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Figure 2: B3LYP/6-31G**-calculated structures of the stable endo,endo diisocyanate 1 (left) and the unstable ...

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Scheme 1: Ring opening taking place on attempted optimization of the calculated, putative endo,exo isomer of 1...

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Scheme 2: Synthesis of the di(hexylurea) and di(methyl carbamate) derivatives 4 and 5.

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Figure 3: Stereoscopic ORTEP plot of molecule A of the di(hexylurea) derivative 4 with atomic numbering schem...

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Figure 4: Stereoscopic ORTEP plot of molecule B of 4 with atomic numbering scheme. The ellipsoids are drawn a...

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Figure 5: Stereoscopic ORTEP plot of the di(methyl carbamate) 5 showing the atomic numbering scheme. The elli...

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Figure 6: The lowest-energy calculated structure of 4 (B3LYP/6-31G**; for other conformers and full details s...

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Figure 7: Calculated structure of 5 (B3LYP/6-31G**). Bond lengths are given in Å and angles in degrees. For a...

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Scheme 3: Synthesis of bis-crown ether diamides 7.

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Figure 8: Calculated structure of 7a-a (B3LYP/6-31G**). Bond lengths are given in Å and angles in degrees. Fo...

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Figure 9: Calculated structure of 7b-a (B3LYP/6-31G**). For other conformers (7b-b and 7b-c) and full details...

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Published 02 Jan 2015

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Synthesis of functionalized macrocyclic derivatives of trioxabicyclo[3.3.0]nonadiene

Sabine Leber,
Gert Kollenz and
Curt Wentrup

Beilstein J. Org. Chem. 2012, 8, 738–743, doi:10.3762/bjoc.8.83

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Scheme 1: Synthesis of macrocyclic bisdioxine derivatives (R,S-form of 4 and S-form of 5 shown; see Supporting Information File 1 for deta...

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Scheme 2: Synthesis of the 1,2,4-trisubstituted aryl derivatives.

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Scheme 3: Synthesis of the 1,2,3-trisubstituted aryl derivatives.

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Scheme 4: Synthesis of the tetraoxaadamantane derivative 14.

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Published 15 May 2012

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