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He and his co-workers prepared (II), the acyloin of [10]paracyclophane, from the diester prepared 18 years previously by Ruzicka et al. (34), who were then interested in pyrolysis of diacids. Though the diacid pyrolysis failed, the acyloin condensation of the diester (III) (II) (ΠΙ) gave (II) (70%). (Remember, however, that this is a somewhat unfair comparison of a 9- vs. ) At the same time Wiesner was interested in forming paracyclophanes by dehydrogenation of Diels-Alder adducts but found the method too laborious and of use possibly only for those systems which could not be formed by the acyloin cyclization.

The more highly substituted these species are, the more likely they are to suffer rearrangement. Thus, although aluminum bromide had been shown to be superior to aluminum chloride as a Friedel-Crafts catalyst, it was felt that the former might be more likely to promote the chances of alkyl rearrangements and so it was not used, the aluminum chloride catalyst being employed instead. As expected, (LI) with η = 2-6 gave the orthocyclized ring (LII), though in varied yields. With η = 1 and above, the meta-bridged derivatives (LIII) with η = 7-10, 13, and 15 were formed, as shown in Table II.

3) The distance between the rings, in any state of saturation, is too great to allow for transannular migration of hydrogen and so the stereochemistry of the reduction must be retained as defined in reason (2). 4]paracyclophane acyloin and esterification of this diacid product gave a diester. This diester differed from one which had been obtained from the reduction of the aromatic diester and which also had, when tried alone, failed completely The Acyloin Cyclization Method 35 to undergo an acyloin cyclization.

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