Aluminum Cyclohexoxide1

Al(OCy)3

[-]  · C18H33AlO3  · Aluminum Cyclohexoxide  · (MW 324.42) (Al)

[7429-90-5]  · Al  · Aluminum Cyclohexoxide  · (MW 26.98) (CyOH)

[108-93-0]  · C6H12O  · Aluminum Cyclohexoxide  · (MW 100.18)

(reducing agent for anthraquinone-related ring systems)

Preparative Method: prepared in situ from Aluminum in refluxing cyclohexanol.2

Handling, Storage, and Precautions: use in a fume hood. The reagent should be freshly prepared just prior to use. Many aluminum alkoxides are extremely irritating to skin, eyes, and mucous membranes and should be handled with appropriate caution. Contact via inhalation route is particularly hazardous.

Reduction.

The reagent has been used by several groups for the reduction of anthraquinone and related derivatives to the corresponding anthracene ring systems under what are essentially Meerwein-Ponndorf-Verley reduction conditions.1 Thus treatment of anthraquinone2 or tetramethylanthraquinone3 with the reagent in boiling cyclohexanol afforded anthracene and 2,3,6,7-tetramethylanthracene, respectively, in good yield (eq 1).

The polycyclic aromatic hydrocarbons benz[a]anthracene4 and 2,3,6,7-dibenzanthracene (pentacene)5 have been prepared in a similar fashion (eqs 2 and 3).


1. Wilds, A. L. OR 1944, 2, 221.
2. Coffey, S.; Boyd, V. JCS 1954, 2468.
3. Hinshaw, J. C. OPP 1972, 4, 211.
4. Ahmed, F. U.; Rangarajan, T.; Eisenraum, E. J.; Keen, G. W.; Hamming, M. C. OPP 1975, 7, 267.
5. Bruckner, V.; Karczag, A.; Kormendy, K.; Meszaros, M.; Tomasz, J. TL 1960, 5.

Gary W. Morrow

The University of Dayton, OH, USA



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