1-tert-Butoxycarbonyl-1-tosyl-hydrazine as reagent for the synthesis of substituted hydrazines with a secondary alkyl group

✍ Scribed by Leif Grehn; Ulf Ragnarsson

• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 626 KB
• Volume: 55
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(99)00156-8

✦ Synopsis

Catalytic hydrogenolysis of l-Boc-l-Ts-2-Z-hydrazane furnished l-Boc-l-Ts-hydrazine as a stable crystalline solid. Although its nacleophilicity is considerably suppressed in comparison with that of non-or monoacylated hydrazines, it reacted under various conditions with a representative set of ketones to give file corresponding hydrazones in high yields. The aliphatic hydrazones were readily reduced to hydrazines with NaBI-L, whereas the aromatic analogues for smooth reduction required the more powerful NaBH3CN. With one exception all the new compounds were crystalline and stable under normal conditions. The new reagent and an alkylated derivative retained satisfactory reactivity towards activated isocyanates to provide acyl ureas. Some characteristic features of the NMR-and IR-spectra of these novel compounds are briefly discussed.