An Efficient Method for the Protection of Aromatic Amines with Benzostabase and Its Utility in Anionic Aromatic Transformations

In celebration of Professor Philip J. Parsons 60^th birthday and his outstanding contributions to organic chemistry

Abstract

Herein we describe an efficient and generally applicable method of protecting a diverse series of aromatic amines with the ‘benzostabase’ group. We also demonstrate its efficient use in aromatic anionic chemistry including its utility in the anionic ortho Snieckus–Fries rearrangement.

Key words

benzostabase - stabase - in situ protection - directed ­ortho Metalation - anionic ortho Snieckus–Fries rearrangement

• References and Notes

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HMPA, elevated temperature, and long reaction times required to install the ‘benzostabase’ group, see ref. 8. For elevated temperatures, long reaction times, see:
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