The synhses and phcbchmical mactbns of oxime m of ethyl 4,4dlmethyl+ oxopent-2+noate and ethyl 2,4,4-trimsthyl+oxo-2-enoate are described. The former compound undergoes E-Z\_ oftheC=CbondwhllethelaUertearrangesbytheazadl+methans reactlontoafforda cydopropene derlvatlve.
The aza-di-π-methane rearrangement of β-γ-unsaturated oximes
✍ Scribed by Diego Armesto; Ana Ramos; Elena P. Mayoral
- Publisher
- Elsevier Science
- Year
- 1994
- Tongue
- French
- Weight
- 343 KB
- Volume
- 35
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
Alihough preview stu&s have shown that acyclic j3.r_unsaturated oximea and oxime ethers do not undergo the aza-dl-mmethane {ADPM) rmrrangewmt. the Z-nu~l~,4dipAm~-2-~nylb~-3-~1 oxiww Sm. its wwhyl ether 51 and the 2,2.4,4-tetraphenylbnt-3-enal oxime I4 give the correapondhg cydopropyl derbatives &,8b and IS by the ADPM path, tn a remtion that Is controfled by the stab&y Opthe tntennediate f3-bira&al.
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