N'-Isopropylidene-2-nitrobenzenesulfonohydrazide

Typical Procedure: Synthesis of (E)-3,7,11-trimethyldodeca-1,6,10-triene (Table 1, Entry 1)
Diethyl azodicarboxylate (74 μL, 0.47 mL) is added dropwise to a mixture of IPNBSH (1, 122 mg, 0.474 mmol), trans,trans-fanesol (0.100 mL, 0.393 mmol) and triphenylphosphine (124 mg, 0.473 mmol) in anhydrous THF (9.0 mL) at 0 °C under an argon atmosphere. After 5 min, the reaction mixture is allowed to warm to 23 °C. After 20 min, a mixture of trifluoroethanol and water (1:1, 4.5 mL) is added to the reaction mixture. After 3 h, the reaction mixture is suspended between diethyl ether (25 mL) and water (25 mL), and the aqueous layer is extracted with diethyl ether. The combined organic layers are dried over anhydrous sodium sulfate, filtered, and concentrated. The residue is purified by flash column chromatography on silica gel (eluent: pentane) to give the desired triene (71 mg, Y. 87 %).

Reference

• N-Isopropylidene-N'-2-nitrobenzenesulfonyl hydrazine, a reagent for reduction of alcohols via the corresponding monoalkyl diazenes
  • M. Movassaghi, O. K. Ahmad, J. Org. Chem. 2007, 72, 1838.