Cyclobutanone → tert-Butyl cyclobutylidenecarbazate

Participants

Reaction Steps

A reaction mixture of cyclobutanone (7.01 g, 100 mmol) and tert-butyl hydrazinecarboxylate (13.22 g, 100 mmol) in hexane (100 mL) was heated under reflux for 2 hours. After cooling down, a precipitate was formed and collected. It was then triturated with isopropanol (5 mL) and hexane (50 mL) to give a white solid as final product tert-butyl 2-cyclobutylidenehydrazinecarboxylate (13.5 g, 73.3 mmol, 73.3% yield). 1H NMR (500 MHz, CHLOROFORM-D) δ ppm 1.50 (s, 9H) 1.96-2.08 (m, 2H) 2.75-2.84 (m, 2H) 2.93-3.05 (m, 2H). MS m/z 207 (M+Na+), Retention time: 1.420 min. (acid).

Provenance & Evidence