propyl) substrate. The initial reactant and all of the intermediates that will react with solvated electrons protect the electron-free zone until their chemistry is complete. It is after complete reduction that the boundary of the mixing process is advanced with more solvated electrons, and the same chemistry continues at or near the new boundary. The visualization of this in chemical terms is that on the time scale of these reactions the substrate finds it environment as either of two extreme situations, electron-free or electron-rich (see ref 6 and 7).We propose that this may be another example of unusual chemical observations that may be accounted for by distortions in the product distributions that are the result of nonhomogeneous chemistry rather than the intervention of unusual reaction mechanisms or intermediates. [6][7][8] Acknowledgment. We thank Mr. B. Weber for assistance in obtaining 500-MHz NMR spectra and Ms. M. Chan for the GC/MS work. Also we thank Professors J. F. Bunnett and A. Oku for helpful discussions concerning this work.Registry No. I,
The cationic cyclocodimerization of 1-(4-vinylnaphthyl)-3-(p-vinylphenyl)propane and l,3-bis(4-vinylnaphthyl) propane with 2-phenylpropene, indene, 1,1-diphenylethylene, and styrene gave [3.3]paracyclo(l,4)naphthalenophanes and [3.3](l,4)naphthalenophanes, respectively, in 11.5-53.6% yields. From the structures
Das Tetrachlor‐dicyclopropyl‐ethan (Ia) liefert bei der Reduktion mit Na bzw. Li die Halogenfreie Verbindung (Ib) neben partiellen Reduktionsprodukten (ll).
Die durch Protonierung der Bis‐ (p‐vinyl‐phenyl)‐alkane (I) gebildeten kationischen Spezies werden von Olefinen (II) bzw. (V) unter Bildung der Paracyclophane (III)+(IV) bzw. (VI) + (VII) abgefangen; die analog mit den Olefinen (VIII) bzw. (IX) gebildeten Primärprodukte können nicht getrennt werden; sie werden erst nach ihrer Hydrierung isoliert [→(X) + (XI); keine präparativen Angaben].
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