Zwitterion mediated cocyclo-oligomerization of small ring ethers. Cycloadditions to a spiroanellated bicyclopropyl unit

Abstract
The diene (1) reacts with tetracyanoethylene in the presence of oxirane or oxetane to yield the macrocyclic 1:1:2 cocycloadducts (7) and (8) respectively; only small amounts of the normal [4 + 2] cyloadduct (2) are formed in any solvent, whereas the abnormal benzocyclo-octene derivative (3) is obtained in 1,4-dioxane almost exclusively.

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