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Extra resources for Advanced Problems in Organic Reaction Mechanisms
Advanced Problems inOrganic Reaction Mechanisms 39 Suggest a mechanism for the transformation of 2 into 3. n. R. : o ..... Ph" Me 1 o ..... (O'1 O ~- 69. A Primary Nitroalkane to Carboxylic Acid Transformation The Nef oxidation of nitroalkanes is a valuable method for the preparation of aldehydes and ketones. French workers have now shown that primary nitroalkanes, used as such or generated in situ from the corresponding bromides, can be oxidised directly to carboxylic acids. Yields are generally excellent and the conditions are very mild; acids, esters, alkenes, a TMS-protected alkyne, alcohols, THP ethers, and an imide were unaffected.
O O O Me O NH 2 Me 1 2 R = PhCH 2 74. Intramolecular Schmidt Reaction In a one-pot process which has been described as an intramolecular Schmidt reaction it has been shown that treatment of ketals or enol ethers of 1,5-azidoketones with Lewis or protic acids followed by sodium iodide in acetone results in formation of lactams in 68-95% yield. Give a mechanism for this reaction, a representative example of which is shown. O Me 1) CH 2C12/TFA N3 2) evaporate ~ 3) NaI/acetone 72% Advanced Problems in Organic Reaction Mechanisms 75.
It was subsequently rapidly established, however, that while the condensation of the phthalimide with the dianion was fully reproducible (almost quantitative crude yield), the structure of the product was not 1 as claimed. It was shown that the correct structure for the 26 Advanced Problems in Organic Reaction Mechanisms condensation product was 3. phthalazinone 2. Moreover, 3 did indeed react with hydrazine to give the Give mechanisms for the formation of 3 and the conversion of 3 into 2. Show also that acceptable mechanisms can be drawn for the formation of 1 and for its conversion into 2.
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