All reactions were performed under an atmosphere of nitrogen unless stated otherwise. Tetrahydrofuran (THF) was distilled from sodium benzophenone ketyl. Hexanes and dichloromethane were distilled under nitrogen. Anilines were commercial samples (Aldrich) used without additional purification.Silica gel plates were 250 µm thick, 40 F 254 grade from EM Science. Silica gel was grade 60 (230-400 mesh) from EM Science. 1 H and 13 C NMR spectra were obtained at 400 and 100 MHz, respectively. IR assignments have 2 cm -1 resolution.Benzyltriethylammonium dichloroiodate (2) from iodine. Commercial bleach (5.25% NaClO, 100 mL, 80 mmol) was added to iodine (20.32 g, 80 mmol), water (200 mL) and concentrated hydrochloric acid (100 mL) contained in an Erlenmeyer flask sitting in an ice bath at such a rate as to keep the temperature below 20 ºC. Toward the end of the bleach addition, the bleach was added dropwise until the endpoint manifested by the disappearance of the brown coloration of iodine was reached. Then, 10% aqueous NaI was added dropwise to restore the barely visible brown coloration and the resulting orange solution was gradually introduced into a solution of benzyltriethylammonium chloride (36.4 g, 160 mmol) in water (50 mL). The resulting light-yellow precipitate was collected by filtration, washed with water (100 mL, 3X)
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.