Nonaromatic 1.3-dioxygenated compounds are susceptible to fragmentation, if one of the oxygen substituents behaves as a nucleofuge'). Whereas our knowledge and experience have indicated that dioxiranes separated by a methylene bridge do not generally undergo CC bond cleavage, an exceptional case was discovered in that 1, 2: 4, 8-diepoxy-p- menthane (terpinolene diepoxide, 1) was rearranged to yield the 3-oxacyclohexanone 2.
