What is the mechanism for ozonoide formation?

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There are three main steps in the mechanism of ozonide formation:

  1. Ozone adds to the alkene to form a molozonide
  2. The molozonide decomposes into two fragments
  3. The fragments recombine to form the ozonide

Step 1

The first step is a 1,3-dipolar cycloaddition of ozone to the alkene. This forms the first intermediate — a molozonide or 1,2,3-trioxolane.

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Step 2

The molozonide decomposes to give a carbonyl oxide and a carbonyl compound:

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Step 3

Like ozone, the carbonyl oxides are 1,3-dipolar compounds.

They undergo 1,3-dipolar cycloaddition to the carbonyl compounds with the opposite regiochemistry.

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The product is the "normal" ozonide — a 1,2,4-trioxolane.

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