Iodine → Di-(2,4-dinitrobenzyl) disulfide

Participants

Reaction Steps

A solution of iodine (0.321 g, 1.26 mmol) and 2,4-dinitrobenzyl mercaptan (0.493 g, 2.3 mmol) in dichloromethane (25 cm3) was stirred at room temperature ovemight. More dichloromethane (25 cm3) was added and the products were washed with 0.2 mol dm-3 sodium hydrogen sulfite (20 cm3), water (20 cm3) and saturated aqueous sodium hydrogen carbonate (20 cm3). The dried (MgSO4) organic layer was concentrated under reduced pressure and the residue was crystallized from absolute ethanol to give di-(2,4-dinitrobenzyl) disulfide 19 (0.402 g, 82%) (Found: C, 39.4; H, 2.4; N, 13.0. C14H10N4O8 S2 requires: C, 39.4; H, 2.4; N, 13.1%), m.p. 108°-109° C.; δH [CDCl3 ] 4.22 (4 H, s), 7.66 (2 H, d, J 8.5), 8.46 (2 H, dd, J 2.4 and 8.4), 8.91 (2H, d, J2.4);δC [CDCl3 ] 40.0, 121.1, 127.5, 133.9, 139.4, 147.4, 148.0.

Provenance & Evidence