Aspects of the addition of iodine(I) azide to alkenes

Abstract

The corresponding peak in the spectrum of (7) should read 6 4.05 not 6 4.50 as recorded.2

Iodo-azide adducts of exocyclic alkenes; structure and solvolysis

“…When the addition of iodine@) azide to camphene was carried out in dichloromethane rather than in acetonitrile, the overall yield of the adducts (48) and (50) decreased and the vinyl iodide (46) became the major product, possibly reflecting a change in the nature of the reagent in this solvent. 28 The current results indicate that the lack of regio-and stereo-selectivity observed for the addition of iodine(1) azide to 3-methyl-A2-steroids,l 3-tbutylcyclohexene,29 and 3-methoxycyclohexene may be due to competition between ionic and radical pathways; this possibility is presently under investigation. Solvolyses of certain vic-iodo-azides were found earlier to be regio-and stereo-~elective,~~ the observed retention of configuration being explained in terms of neighbouring-group participation by the azide group to give an N-diazonioaziridine 3o (cf.…”

“…geminal to the primary iodide in compound (29) did, in fact, resonate slightly upfield from those (FH 3.11) geminal to the primary azide in compound (28) , but the chemicalshift difference was insufficient to distinguish clearly between a primary azide or iodide on the basis of these data alone. In contrast, the large difference between the 13C n.m.r.…”

“…l-Azidonzethylcyclohexane (28) .-The above toluene-psulphonate (2.20 g, 8.21 mmol) in anhydrous hexamethylphosphoric triamide (1 1 ml) was treated with sodium azide (0.82 g, 12.62 mmol) a t 80 "C for 3 h. The solution was poured into water and extracted with diethyl ether. The extract was worked up to give an oil (1.07 g) which, on distillation, gave the cyclohexane ( 28 (C-1); n?/z 224 (hi"-') and 97 (&I + ' -i).…”

Vicinal Diamination of Terminal Olefins

“…± We wish to report here a convenient and efficient threestep process with conventional and commercially available reagents. It is exemplified by the following preparation: 10-(benzyloxy)dec-1-ene (1) reacted at 08 with the IN 3Ń aN 3 complex [6] to give 2-azido-10-(benzyloxy)-1-iododecane (2; Scheme). ± The IN 3´N aN 3 complex was prepared from iodine monochloride and NaN 3 according to the method of Hassner and co-workers [7].…”

Regiospecific Azidoiodination of Alkenes with Sodium Periodate, Potassium Iodide, and Sodium Azide: A High-Yield Synthesis of β-Iodoazides

“…However, this yield was increased to 95% when the stoichiometry of sodium azide was increased to three equivalents (Scheme 1). 15 This prompted us to explore the effectiveness of the sodium periodate, potassium iodide, and sodium azide system in the 1,2-azidoiodination of several alkenes. This new azidoiodination procedure was indeed found to be quite general for a variety of olefins and the results of this study are summarized in Table 1.…”