Solid-state reactivity of the hydrazine-hydroquinone complex

Isolation and structural characterization of the elusive 1 : 1 adduct of hydrazine and carbon dioxide

“…The solid hydrazine (1) will thus be beneficial for the extensive application of hydrazine to many organic syntheses, and this will not only enhance the selectivity but also reduce organic wastes. [17][18][19] In summary, our solid hydrazine is a 1 : 1 adduct of hydrazine and CO 2 and is very stable. Moreover, its reactivity is similar to that of liquid hydrazine and exhibits better selectivity due probably to the absence of water.…”

Isolation and structural characterization of the elusive 1 : 1 adduct of hydrazine and carbon dioxide

“…The solid hydrazine (1) will thus be beneficial for the extensive application of hydrazine to many organic syntheses, and this will not only enhance the selectivity but also reduce organic wastes. [17][18][19] In summary, our solid hydrazine is a 1 : 1 adduct of hydrazine and CO 2 and is very stable. Moreover, its reactivity is similar to that of liquid hydrazine and exhibits better selectivity due probably to the absence of water.…”

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

“…[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.…”

Manual grinding mechanochemistry: An emerging tool for environmentally benign and sustainable synthesis

“…As a source of hydrazine, the hydrazine-hydroquinone 1:1 compound, which is a stable solid at ambient conditions, was employed to synthesize various azine compounds by Kaupp and Schmeyers. 26 The solid-state reaction was carried out by ball-milling the compound with a solid aldehyde, yielding a mixed powder of the desired azine and hydroquinone. The two products can be separated by extracting the powder with water, as hydroquinone is soluble in water while the azine compound is not.…”

Isolation and structural characterization of the elusive 1 : 1 adduct of hydrazine and carbon dioxide

“…The solid hydrazine (1) will thus be beneficial for the extensive application of hydrazine to many organic syntheses, and this will not only enhance the selectivity but also reduce organic wastes. [17][18][19] In summary, our solid hydrazine is a 1 : 1 adduct of hydrazine and CO 2 and is very stable. Moreover, its reactivity is similar to that of liquid hydrazine and exhibits better selectivity due probably to the absence of water.…”

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

“…[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.…”

Manual grinding mechanochemistry: An emerging tool for environmentally benign and sustainable synthesis

“…As a source of hydrazine, the hydrazine-hydroquinone 1:1 compound, which is a stable solid at ambient conditions, was employed to synthesize various azine compounds by Kaupp and Schmeyers. 26 The solid-state reaction was carried out by ball-milling the compound with a solid aldehyde, yielding a mixed powder of the desired azine and hydroquinone. The two products can be separated by extracting the powder with water, as hydroquinone is soluble in water while the azine compound is not.…”

Isolation and structural characterization of the elusive 1 : 1 adduct of hydrazine and carbon dioxide

“…The solid hydrazine (1) will thus be beneficial for the extensive application of hydrazine to many organic syntheses, and this will not only enhance the selectivity but also reduce organic wastes. [17][18][19] In summary, our solid hydrazine is a 1 : 1 adduct of hydrazine and CO 2 and is very stable. Moreover, its reactivity is similar to that of liquid hydrazine and exhibits better selectivity due probably to the absence of water.…”

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

“…[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.…”

Manual grinding mechanochemistry: An emerging tool for environmentally benign and sustainable synthesis

“…As a source of hydrazine, the hydrazine-hydroquinone 1:1 compound, which is a stable solid at ambient conditions, was employed to synthesize various azine compounds by Kaupp and Schmeyers. 26 The solid-state reaction was carried out by ball-milling the compound with a solid aldehyde, yielding a mixed powder of the desired azine and hydroquinone. The two products can be separated by extracting the powder with water, as hydroquinone is soluble in water while the azine compound is not.…”