Acylation of a Cycloalkane Remote Functionalization

Treatment of Decalin with acetyl chloride and aluminum chloride in ethylene chloride as solvent gives a complex mixture of products as shown (15). By variation of the reaction parameters, however, it is possible to maximize the yield of the remarkable reaction product, 10 j3-vinyl-/m j-Decalin l/8,r oxide (5). This vinyl ether undoubtedly 

The vinyl ether is quite stable and can be converted readily to a variety of disubsti-tuted trans-Decalins. Its preparation and conversion to a derivative are given in the procedures. 

CARBON-CARBON BOND FORMATION BY MISCELLANEOUS REACTIONS 

The vinyl ether may be further purified by dissolving it in 15 ml of dry ether and adding a solution of 0.25 g of lithium aluminum hydride in 10 ml of dry ether. The mixture is refluxed for 30 minutes, and excess hydride is destroyed by addition of ethyl acetate (1 ml). Ice-cold dilute (0.5 N) sulfuric acid (25 ml) is gradually added to the cooled mixture, the ethereal layer is rapidly separated, the aqueous layer is extracted once with 10 ml of ether, and the combined ethereal solution is washed once with water and dried over potassium carbonate. Removal of the solvent, followed by distillation of the residue affords about 85% recovery of the pure vinyl ether, bp 102-10376 mm, 1.5045. 

The vinyl ether prepared above (4.5 g) is dissolved in 30 ml of ether and mixed with 60 ml of 1 A sulfuric acid in a 250-ml flask equipped with a magnetic stirrer and a condenser. The mixture is gently refluxed with stirring for 2.5 hours, and the cooled 

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