Iodine → 1-Iodotetratriacontane

Participants

Reaction Steps

To a solution of 44.8 g. (0.15 mole) of Cp2ZrCl2 in 800 ml. tetrahydrofuran under Argon was added 24.7 g. (0.086 mole) of NaAlH2 (OCH2Ch2OCH3)2 in benzene via syringe. After stirring 2 hours at room temperature, 36.8 g. (0.077 mole) of the olefin, 17-tetratriacontene, was added and the mixture kept at 40° C. for 7 days. After cooling in an ice bath, solid iodine (34.0g., 0.134 mole) was added. The mixture was filtered and the solvent removed in vacuum. NMR analysis indicated an olefin:iodide ratio of 25:75. The residue was dissolved in hexane and percolated through dry silica gel to remove impurities. Recrystallization from hexane gave 13.0 g. pure iodide, m.p. 75°-6° C. and 14.4 g. of a 58:42 olefin:iodide mixture.

Provenance & Evidence