Science of Synthesis

Wicha, J., Science of Synthesis, (2009) 48, 126.

Aldehydes and ketones are capable of forming their tosylhydrazone derivatives on treatment with tosylhydrazine. The reaction is usually carried out in anhydrous methanol, ethanol, or diethyl ether,[‌163‌] and occasionally in other solvents, such as glacial acetic acid.[‌164‌] Yields depend largely on the steric shielding of the carbonyl group: reactions of aldehydes and unbranched aliphatic ketones are essentially quantitative, whereas formation of the tosylhydrazone derivative of sterically hindered or non-electrophilic ketones may be problematic. In general, tosylhydrazones are moderately stable on storage, although many of these compounds are crystalline.

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References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) M 8e, 88.