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Updated: Aug 16, 2025

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
Published on: April 19, 2019
Phenyloxycarbonyl (Phoc) Carbamate: Chemioselective Reactivity and Tetra-n-butylammonium Fluoride Deprotection Study
Florent Huguenot1,2, Michel Vidal1,2,3
1CNRS UMR 8038 CiTCoM, Université de Paris, Faculté de Pharmacie de Paris, 4 Avenue de l'observatoire, Paris 75006, France.
Abstract:
We present the results of the chemoselective reactivity of phenylcarbamates. Phenylcarbamates of primary amines are reactive to form urea, and phenylcarbamates of secondary amines can be used as tags due to the existence of rotamers. Moreover, deprotection attempts to to recover the primary amines in use of a catalytic amount of TBAF show the possibility of obtaining the symmetrical urea from the corresponding phenylcarbamate. We have begun the study of the transformation of Phoc carbamates into the corresponding free amines by TBAF. We present here our most significant results concerning the sensitivity of this reaction in terms of the solvent and substrate.
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