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Griesbeck, A. G.; Sokolova, T., Science of Synthesis, (2008) 37, 466.
Ring opening of oxetanes can proceed by several processes and leads to synthetically interesting saturated or unsaturated products: Nucleophilic ring opening by hydrogen peroxide gives 3-hydroperoxy alcohols, which can be converted into 1,2-dioxolanes;[149] ring opening with dinitrogen pentoxide gives 1,3-dinitrate esters;[150] and γ-fluoro alcohols are available from oxetanes and silicon tetrafluoride.[151] Hydrogenolysis of 3-siloxy-substituted oxetanes in methanol with hydrogen gas and a palladium catalyst gives 1,2-diols;[152] reductive ring opening with lithium tri-tert-butoxyaluminum hydride leaves the siloxy group intact.[153] The synthesis of 1,3-methoxy alcohols can be achieved by treatment with ammonium cerium(IV) nitrate in methanol.[154] Oxetan-3-ylmethanols are reagents for introducing ortho ester protecting groups to carboxylic acids.[155] An improved reagent for this process is (2,2,3-trimethyloxetan-3-yl)methanol (187), which gives the ortho esters 188 (Scheme 67).[156]
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References
[149] | Mee, M.; Meeeeeeeee, M. M.; Mee, M.; Meeeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[150] | Meeeeee, M.; Meeeee, M. M.; Meee, M. M.; Meeeeeee, M. M., Meeeeeeeeee, (8888) 88, 8888. |
[151] | Meeeeee, M.; Meeeeeee, M.; Meeeeeee, M., Meeeeeeeeeee, (8888) 88, 888. |
[152] | Meee, M., Meeeeee Mee., (8888), 8888. |
[153] | Meee, M.; Möeeeee, M., Meee. Mee., (8888) 888, 8888. |
[154] | Meee, M.; Meeee, M.; Meeeeee, M.; Meeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[155] | Meeee, M. M.; Meee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[156] | Meeee, M.-M., Mee. Meee., (8888) 8, 888. |
[157] | Mee, M.; Meee, M.-M., Meeeeeeee, (8888), 8888. |
[158] | Me, M. M.-M.; Me, M. M., Meeeeeeeeee, (8888) 88, 8888. |
[159] | Meeeeee, M. M.; Meeeeeeee, M. M.; Méeee-Meee, M., M. Meee. Meee. M, (8888) 888, 8888. |
[160] | Méeee-Meee, M.; Meeeeeeee, M. M.; Meeeeee, M. M., M. Mee. Meee., (8888) 88, 88888. |
[161] | Méeee-Meee, M.; Meeeeee, M. M.; Meee, M.; Meeeeeee, M.; Meeeeeeee, M. M., Meeeeeeee. Meeeeeeee. Mee., (8888) 8, 88. |
[162] | Meeeeeee-Meeeee, M.; Meeeeeee, M.; Meeeeeee, M.; Meeeeeeee-Meáeee, M.; ee Meeeeee, M. M., Meeeeeeeeee Meee., (8888) 88, 88. |
[163] | Meee, M. M.; Mee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[164] | Meeee, M.; Meeeeeeee, M.; Meeee, M.; Meeee, M.; Meeee, M.; Meeeee, M.; Meee, M., Meeeeeeeeeeeee, (8888) 88, 8888. |
[165] | Meeeeeeee, M.; Meeeeeeöe, M.; Meee, M., Meeeeeeeeeeeee, (8888) 88, 8888. |
[166] | Me, M.; Mee, M.; Meee, M.; Mee, M.; Mee, M.; Me, M.; Mee, M., Meeeeeeeeeeeee, (8888) 88, 8888. |
[167] | Meeeeeee, M.; Meee, M., Meeeeeeeeeeeee, (8888) 88, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 8/8, 888.
- 8.Meeeee-Meee, (8888) 8/8e8, 8888.