Spiro-oxirane ring derivatives

In an analogous manner, treatment of 4-(2-haloethyl)-phenols and -l-naphthols " with bases produces spiro[2.5]octa-4,7-dien-6-ones and their benzo analogues, respectively. The basic treatments of jS-oxiranyl ketones , esters (equation 13) , nitriles , sulfones and alkynes affords 2-(hydroxymethyl) cyclopropyl derivatives, usually as the sole cyclization product. The cyclization occurs regiospecifically by the intramolecular attack of the anion on the y-carbon in the oxirane ring. Attack of the anion on the 5-carbon in the oxirane, which should lead to the formation of cyclobutanols, usually does not take... 

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