Solid-state reactivity of the hydrazine-hydroquinone complex

Kaupp, Gerd; Schmeyers, Jens

doi:10.1002/1099-1395(200007)13:7<388::aid-poc278>3.0.co;2-h

Cited by 19 publications

(9 citation statements)

References 20 publications

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“…The always-found anisotropic feature formation verifies chemical reaction also in the absence of grinding or milling. [3][4][5][6][7] All of these reactions are chemically driven and preparatively used. Exhaustive reviews are available for >1000 solid-state molecular reactions that are waste-free with 100% yield 8 and for stereoselective ones.…”

Section: Molecular Solid-state Chemistry Versus Mechanochemistrymentioning

confidence: 99%

“…49,50 It is not clear if that is only in part mechanochemistry, because Ag 3 Sn is very ductile, but Ag 2 O has an infinite cuprite structure (Ag-O distances: 2.0438 A ˚) that might also be cracked after penetration into the ductile intermetallic phase. An AFM study [3][4][5][6][7] would be helpful in this respect. The plasma formation upon milling of infinite oxides can also be used for reaction with salts.…”

Section: Milling Of Further 3d-covalent Structuresmentioning

confidence: 99%

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Mechanochemistry: the varied applications of mechanical bond-breaking

2009

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Section: Molecular Solid-state Chemistry Versus Mechanochemistrymentioning

confidence: 99%

Section: Milling Of Further 3d-covalent Structuresmentioning

confidence: 99%

Mechanochemistry: the varied applications of mechanical bond-breaking

2009

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“…[80] Further systems have been studied according to the same technique and prove equally well that solid-solid reactions are driven by chemistry and that the use of milling is only necessary for creating repeated contacts of micronized crystals for a rapid completion of the reaction. Figure 9 is discussed above, further published images cover the rearrangement of benzopinacol with p-toluenesulfonic acid (0.1 and 0.5 mm distance), [22] hydrazine-hydroquinone complex with p-hydroxybenzaldehyde condensation (0.1 mm distance, both crystals measured), hydrazine-hydroquinone complex with 4-dimethylaminobenzaldehyde condensation (1 mm distance), [81] and thiourea with phenacylbromide cascade to give the 2-amino-4-phenylthiazole hydrobromide (0.5 mm distance). [82] All of these are solid-solid reactions and the features correlate with the crystal structures.…”

Section: Molecular Solid-state Chemistry Versus Mechanochemistrymentioning

confidence: 96%

Waste‐free synthesis and production all across chemistry with the benefit of self‐assembled crystal packings

Kaupp

2008

J of Physical Organic Chem

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A systematic mechanistic discussion of solid-state reactions (intracrystalline, intercrystalline, gas-solid thermal, or photochemical) at local molecular resolution is the basis for industrial sustainable production with waste-free solid-gas and stoichiometric solid-solid reactions at low energy requirement. These profit from the bargain of the self-assembled crystal packing. They rapidly complete to give 100% yield and require no solvent for workup. The basic requirements are thermodynamic feasibility and anisotropic molecular migrations at local pressure or suction in opposition to claims of 'minimal atomic and molecular movements' that do not know gas-solid and solid-solid reactions. Topochemical failures are settled on that experimental basis by atomic force microscopy (AFM), correlation with the crystal packing, scanning near field optical microscopy (SNOM), and nanoscratching. A general three-step phase rebuilding mechanism is derived that provides directions for all experimental situations including stereoregular polymerizations. Heat control in gas-solid equipment and solid-solid small-scale vibration or large-scale rotation ball-mills is essential. If AFM identifies (nano)liquids cooling is required. Also rare cases of surface passivation are detected by AFM. Molecular solid-state chemistry and mechanochemistry are differentiated. Solid-state techniques easily exclude moisture and are able to synthesize hitherto inaccessible compounds. Some of the latter are selected for discussion out of more than 1000 waste-free solid-state reactions in addition to already executed kg-scale productions using reasonably inexpensive starting materials with promise for industrial applications and extensions.

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“…58 The reaction of solid aldehydes or ketones with hydrazinehydroquinone complex in a 2 : 1 ratio provided quantitatively solid mixtures of the azine products and hydroquinone when ball-milled at 25-30 1C for 1-3 h (Scheme 28). 61 Naimi-Jamal, Kaupp and coworkers employed the so-called ''kneading ball-milling'' for partly liquid or sticky stoichiometric carbonyl derivatization reactions with the poorly mixing hydroxylamine hydrochloride and wetted 2,4-dinitrophenylhydrazine. 62 Owing to the potential explosiveness of dry 2,4-dinitrophenylhydrazine, 50 wt% H 2 O was added to wet the crystals.…”

Section: Hydrazone Formationmentioning

confidence: 99%

Mechanochemical organic synthesis

2013

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Recently, mechanical milling using a mixer mill or planetary mill has been fruitfully utilized in organic synthesis under solvent-free conditions. This review article provides a comprehensive overview of various solvent-free mechanochemical organic reactions, including metal-mediated or -catalyzed reactions, condensation reactions, nucleophilic additions, cascade reactions, Diels-Alder reactions, oxidations, reductions, halogenation/aminohalogenation, etc. The ball milling technique has also been applied to the synthesis of calixarenes, rotaxanes and cage compounds, asymmetric synthesis as well as the transformation of biologically active compounds.

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Solid-state reactivity of the hydrazine-hydroquinone complex

Cited by 19 publications

References 20 publications

Mechanochemistry: the varied applications of mechanical bond-breaking

Mechanochemistry: the varied applications of mechanical bond-breaking

Waste‐free synthesis and production all across chemistry with the benefit of self‐assembled crystal packings

Mechanochemical organic synthesis

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