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Sigmatropic Rearrangements of Allyl Amine Oxides The Meisenheimer Rearrangement

3]-Sigmatropic Rearrangements of Allyl Amine Oxides The Meisenheimer Rearrangement [Pg.148]

5-Sigmatropic shifts are not pericyclic because suprafacial overlapping of cyclic p-orbitals is not involved. In these shifts, the orbitals from the breaking bond and the lone pair overlap with the p-orbitals in the TS. These reactions have planar nonaromatic eight-centered cyclic transition states with orthogonal orbital [Pg.148]

Indicate which of the following reactions are orbital symmetry allowed processes and which are forbidden. Also indicate the order of sigmatropic shift for each reaction. Each reaction may take place in one or more steps. Justify your answer. [Pg.151]

Suggest a mechanism for each of the following transformations. More than one step may be involved in each case. Predict the major and minor products when more than one product is expected. [Pg.152]

Predict the expected product with structure and stereochemistry for each of the following reactions  [Pg.153]




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Allyl amine

Allyl oxide

Allyl rearrangement

Allylic amination

Allylic aminations

Allylic oxidation

Allylic rearrangement

Amine oxides Meisenheimer rearrangement

Amine oxides allyl, -sigmatropic rearrangements

Amine oxides allylic, sigmatropic rearrangement

Amine oxides, allylic, rearrangements

Amines allylation

Amines rearrangements

Meisenheimer

Meisenheimer rearrangement

Of allyl amines

Of sigmatropic

Oxidation oxidative rearrangement

Oxidation rearrangements

Rearrangements of amine oxides

Sigmatropic -rearrangements rearrangement

Sigmatropic rearrangements of amine oxides

The Amines

The oxidation of amines

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