Preparation of Protected Allylic Primary Amines from Allylic Phenyl Selenides

References

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• Closely related observations have been made in the rearrangement of allylic selenides to allylic alcohols. See ref. 5
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• Overman , L. 1976 . J. Am. Chem. Soc. , 98 : 2901 All of the protected amines provided NMR, IR, and low resolution mass spectra in accord with the indicated structures. The BOC and CBZ protected amines in entries 1 and 5 were compared with authentic samples prepared by direct protection of the parent allylic amines. The authentic parent amine for entry 5 was prepared by the method of Overman
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• The reagents 4 and 5 retain appreciable activity after storage for at least several weeks at 25°C. Difficulties were encountered, however, after the reagents were stored for several months at 25°C. A modification of this procedure which circumvents this inconvenience is under investigation and will be published at a later date
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