Bridged Aromatic Compounds by Brandes H. Smith (Eds.)

By Brandes H. Smith (Eds.)

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When the melting point of a mixture of the two was undepressed it was concluded that the higher melting species was a pure substance and the lower a eutectic of two isomers. 5]paracyclophane. At some intermediate point in the hydrogenation of this compound then, the rings turn with respect to each other to create the isomer distribution. 5]paracyclophane obtained by reduction of the aromatic species, there probably exist all three isomers, the cis-cis, cis-trans, and trans-trans, listed in decreasing order.

By an entirely new experimental procedure the yields of (LXIX) were increased (Table IV). 0 there was slowly added an equivalent amount of water, then a large amount of chloroform. 03 m M / h o u r ) t o give the above yields. This further strengthened the idea that time is needed for the acid chloride chain to become conformationally optimized to the form for this substitution. It is also quite possible that this is not the conformation of lowest energy a n d so n o t very highly populated, but that the lowest energy conformation is n o t suited for substitution at any position on the thiophene nucleus.

In all cases the latter catalyst gave superior yields and allowed a faster dropping rate. Thus, the action of AlBr 3 on (XLVI), Preparation 50 η = 8, gave both the monocyclic (XLVIII) and also the dimer (XLIX) (7%). At this time they also reported the highest member of the series of (XLVIII)'s, η = 15 (70%), by using the AlBr 3 catalyst. This yield of 70% was compared to the previously observed maximum of 35% with the aluminum chloride catalyst. Another series of homologous ketones, similar to (XLVII) and (XLVIII), which are possible in the cyclophane area but have not as yet been mentioned are the [«]metacyclophan-l-ones.

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