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38.9.1.5.3 Ozonolysis of Unsaturated Hydroperoxides

DOI: 10.1055/sos-SD-038-00454

Alberti, M. N.; Tzirakis, M. D.; Orfanopoulos, M.Science of Synthesis, (200938505.

Various cyclic 7- to 12-membered hydroperoxy- and hydroxy-substituted spiro-tetraoxacycloalkanes, 142 and 143 respectively, are obtained by ozonolysis of the corresponding unsaturated hydroperoxides 141 in 2,2,2-trifluoroethanol (Scheme 34).[‌103‌] The bridged bicyclic peroxides 145, containing the 2,3-dioxabicyclo[3.3.1]nonane system of yingzhaosu A, are prepared by ozonolysis/cyclization of a series of unsaturated hydroperoxides of type 144. Similarly, ozonolysis of the unsaturated hydroperoxides 146 proceeds smoothly to afford the corresponding bicyclic peroxides 147, in high yields (Scheme 34).[‌104‌] Moreover, 1,2,4-trioxepanes 149 are prepared following a similar procedure from peroxyhemiacetals 148.[‌105‌]

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