Diethylaluminum Iodide


[2040-00-8]  · C4H10AlI  · Diethylaluminum Iodide  · (MW 212.01)

(ethylating agent; catalyst)

Alternate Names: diethyliodoaluminum; diethyliodoalane.

Physical Data: bp 118-120 °C/4 mmHg; d 1.609 g cm-3.

Solubility: sol toluene, benzene.

Form Supplied in: colorless liquid; commercially available, either neat or in toluene solution.

Preparative Methods: by reaction of Triethylaluminum and Aluminum Iodide in THF or benzene.1

Handling, Storage, and Precautions: moisture-sensitive and pyrophoric. Reacts with water to form an explosive and flammable gas. Extremely harmful if vapors are inhaled. The reagent is absorbed through skin. Wear gloves. Corrosive. Air-sensitive; must be stored under inert atmosphere. Use in a fume hood.

Addition to a Carbonyl Group.

In using the reagent to deliver the ethyl group to a carbonyl, there appears to be a preference for equatorial attack on cyclohexanones (eq 1).1 A preference was also noted for 1,2-attack over 1,4-attack (eq 2).

Addition to a Carbanion.

An alkylation-deoxygenation reaction provides an interesting approach to substituted alkenes from epoxides (eq 3).2

Aldol-Type Reactions.

Diethylaluminum iodide-catalyzed reaction of aldehydes with a,b-unsaturated carbonyl compounds provides a useful entry into molecules of the types shown in eqs 4-7.3

Beckmann Rearrangement.

Diethylaluminum iodide is a useful catalyst for conversions of the general type shown in eq 8.4

Related Reagents.

Diethylaluminum Chloride; Dimethylaluminum Chloride; Dimethylaluminum Iodide; Ethylaluminum Dichloride; Methylaluminum Dichloride.

1. Ashby, E. C; Noding, S. A. JOC 1979, 44, 4792.
2. Taniguchi, M.; Oshima, K.; Utimoto, K. TL 1991, 32, 2783.
3. Itoh, A.; Ozawa, S.; Oshima, K.; Nozaki, H. BCJ 1981, 54, 274.
4. Ishida, Y.; Sasatani, S.; Maruoka, K.; Yamamoto, H. TL 1983, 24, 3255.

Bradford P. Mundy

Colby College, Waterville, ME, USA

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