Aluminum chloride decane

Aluminum chloride, 45, 109 with lithium aluminum hydride, in reduction of l,4-dioxaspiro[4 5] decane 47, 37... 

Lithium aluminum hydride, with aluminum chloride, for reduction of 4-f-butylcydohexanone, 47,17 in reduction of 1,4-dioxaspiro[4.5J-decane, 47, 38... 

Aluminum amalgam in reduction of oximinomalononitrile, 48, 2 Aluminum chloride, 46, 109 in conversion of tetramethy 1-1,3-cyclobutanedione to dimethyl-ketene d-lactone dimer, 48, 72 with lithium aluminum hydride, in reduction of l,4-dioxaspiro[4.5 -decane, 47, 37... 

Halides and tosylates. Trevoy and W. G. Brown found that lithium aluminum hydride reduces benzyl iodide and benzyl bromide in high yield at 35° in either diethyl ether or tetrahydrofurane. In tetrahydrofurane at 65°, benzyl chloride and 1 -bromodecane are reduced to toluene and to n-decane, both in 72% yield. Johnson, Blizzard, and Carhart found that lithium aluminum hydride reacts more sluggishly than in other reductions and presented experimental evidence that not all four hydrogen atoms possess adquate reactivity toward alkyl halides. Thus the reaction probably proceeds in at least two steps, the first of which is much more rapid than... 

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