摘要：

The reaction of cycloctene dibromide with silver acetate in dry acetic acid has been shown to yield 3-cycloocten-1-yl acetate, 4-cycloocten-1-yl acetate, cis-1,4-cyclooctanediol diacetate, trans-1,4-cyclooctanediol diacetate and only a small amount of the expected trans-1,2-cyclooctanediol diacetate. The structures of the cycloctenyl acetates have been elucidated by ozonolysis of the corresponding phenylurethans and reduction of the ozonides with sodium borohydride, followed by treatment with phenyl isocyanate to form the corresponding octanetriol tris-phenylurethans. Authentic specimens of 1,3,8- and 1,4,8-octanetriol tris-phenylurethans have been prepared for comparison. The course of the reactions leading to the abnormal products listed above is interpreted as resulting from the spatial proximity of opposite sides of the eight-membered ring.

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