AUyl iodide

Place 56 g. of clean sodium, cut into small pieces, in a 500 ml. round-bottomed flask fitted with two 25 or 30 cm. double surface condensers in series. Weigh out 136 g. (72 ml.) of freshly distilled allyl iodide, b.p. 99-101° (Section 111,39). Introduce about one quarter of the aUyl iodide through the condensers. Warm the flask gently until the sodium commences to melt and immediately remove the flame. A vigorous reaction sets in and a liquid refluxes in the condensers. Add... 

E = PhCHO, PhCOCl, aUyl iodide E = PhCH(OH), PhCO, CH2 = CHCH2... 

Preparation This orange cobalt complex is prepared from KCo[P(OCH3)3 ]4 and aUyl iodide in THF (room temperature). 

CH3=CHCHr3l -1- 2Na — CH3=CHCHjCH3CH=CHj + 2NaI AUyl iodide Diallyl... 

The tandem ylide generation/[2,3]-sigmatropic rearrangement can also be performed with sulfur and iodonium ylides and in these cases the reaction can proceed in intermolecular fashion.For example, up to 78% ee has been obtained in the reaction of allyl-2-methylphenyl sulfide (9.129) with aryl diazoacetates such as (9.130) in the presence of the copper catalyst generated with bis-oxazoline (9.07), while the reaction of aUyl iodide (9.132) with ethyl diazoacetate yields product (9.133) with 69% ee using this complex. ... 

Grzybowska, B., Haber, J., and Janas, J. Interaction of aUyl iodide with molybdate catalysts for the selective oxidation of hydrocarbons. J. Catal. 1977, 49, 150-163. 

Doomkamp, C., Clement, M., and Ponec, V. Activity and selectivity patterns in the oxidation of aUyl iodide on the period IV metal oxides the participation of lattice oxygen in selective and total oxidation reactions. Appl Catal. A Gen. 1999,188, 325-336. 

Veratrol (1) AUyl iodide (0.5) Zn (0.015) — Warm 2.5 Methyl eugenyl ether 257... 

An optimum enantioselectivity of 90% and yield of 72% was observed for the aUyl bromide/benzaldehyde system at 5°C. In contrast to ligand 11, this new salen ligand 14 was also able to affect an enantioselective addition of aUyl iodide. Related (3-methallyl halides reacted as smoothly as the allyl halides although the enantioselectivities were lower. To demonstrate the applicability of this methodology to polyketide natural-product synthesis, p-methoxybenzyl (PMB)-protected 3-hydroxypropanal was coupled with aUyl bromide in an excellent enantioselectivity of 92%, albeit in a moderate yield of 69%. Finally, vinyl iodides and triflates were used as substrates, with 2 mol% of Ni(II) required for efficient coupling. The addition of fi-l-iodohex-l-ene to PMB-protected 3-hydroxypropanal afforded the corresponding S-allylic alcohol adduct in 75% ee. A vinyl triflate also... 

Camaggi, C.M., Leardini, R., and Zanirato, R, Photolysis of aUyl iodide in aromatic solvents, /. 

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