Organic Lab Reactions 149

Organic Lab Reactions 149 - the aluminum chloride already...

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144 THE FORMATION OF CYCLIC KETONES TABLE VI— Continued CYCMZATIONS BY THE FBIEDEI/-CBAIT8 STANNIC CHLORIDE METHOD Ring System of Ketones Prepared 4',5-Dimethylene-3,4-benzpyrene o - Yields 98%* Reference 111 * Prepared by the phosphorus pentachlonde method; those without asterisk were made with thionyl ohloride. ALUMINUM CHLORIDE The examples of intramolecular acylation by the use of aluminum chloride in the Friedel-Crafts reaction occur in the literature so fre- quently that no attempt has been made here to enumerate all of them. Table VII includes several different types of arylpropionic and aryl- butyric acids which have been cyclized by this method. The reaction conditions generally seem to be more critical with aluminum chloride than with stannic chloride. Yields, perhaps as a result, are more often hard to duplicate. These facts are doubtless due in part to the greater reactivity of aluminum chloride and to the diffi- culty commonly experienced in obtaining samples of this reagent which do not vary in catalytic effect. A pronounced influence of the grade of
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Unformatted text preview: the aluminum chloride already has been mentioned. In five out of six ring closures, better yields were obtained with stannic chloride than with aluminum chloride. The greater activity of the latter reagent was apparently not necessary in these instances. There 101 Bachmann and Struve, J. Org. Chem., 4, 472 (1939). 102 Baohmann, Cole, and Wilds, J. Am. Chem. Soc, 62, 824 (1940). 103 Burnop, Elliott, and Linstead, J. Chem. Soc, 1940, 727. 104 Baohmann and Edgerton, / . Am. Chem. Soc., 62, 2219 (1940). 106 Baehmann and.Sheehan, J. Am. Chem. Soc, 63, 204 (1941). 106 Bachmann and Sheehan, / . Am. Chem. Soc, 63, 2598 (1941). 107 Bachmann and Struve, J. Org. Chem., 4, 456 (1939). 108 Bachmann and Chemerda, J. Org. Chem., 6, 50 (1941). 1OT (a) Bachmann and Safir, / . Am. Chem. Soc, 63, 855 (1941); (6) ibid., 2601. 110 Bachmann and Carmack, J. Am. Chem. Soc, 63, 2494 (1941). 111 Bachmann and Carmack, J. Am. Chem. Soc, 63, 1685 (1941)....
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This note was uploaded on 11/20/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.

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