Preparation of tetramethylpiperidine-1-oxoammonium salts and their use as oxidants in organic chemistry. A review was written by Merbouh, Nabyl;Bobbitt, James M.;Brueckner, Christian. And the article was included in Organic Preparations and Procedures International in 2004.COA of Formula: C11H21BF4N2O2 This article mentions the following:
The discovery of 2,2,6,6-tetramethylpiperidine-based oxoammonium salts (I; R = oxo, H, OH, NH2, NHAc, OMe, OBz) in 1965 by Golubev et al has led to the synthesis of a number of oxoammonium-based oxidizing agents with diverse properties. However, many of the oxoammonium salts or their precursors are either not com. available or are expensive. Reports of their preparation are spread over 40 yr of literature. This review is a compilation of the most often cited and most practical procedures for their syntheses and includes exptl. details. A large body of work detailing the use of oxoammonium salts as catalytic and stoichiometric oxidants in preparative organic chem. also accumulated over the past four decades. The review of their use, however, will focus on the literature from 1990 to date, excluding the patent literature, as a number of excellent earlier reviews on select aspects of this chem. are available. The goal of this review is to allow organic chemists to prepare and study oxoammonium salts, irresp. of their list prices or com. availability. Oxoammonium salts I are derived from nitroxide free radicals (II) by a one-electron oxidation Nitroxides are generally prepared by oxidation of the corresponding amine 2,2,6,6-tetramethylpiperidine derivatives (III). The α-Me groups are crucial for the stabilization of the oxoammonium salts. A number of 4-substituted tetramethylpiperidine derivatives were used for the synthesis of oxoammonium salts, combined with several counter ions. Oxoammonium salts are potent but selective oxidants. They can either be prepared in situ from a nitroxide by reaction with a secondary oxidant, thus making the nitroxide a catalyst, or they can be used as stoichiometric oxidants. They are versatile oxidants in organic chem. and the mild, transition metal-free reaction conditions and the selectivity of the oxidations recommend these oxidants for wider use. Further, the option for tandem reactions will greatly increase the utility of these reagents. In the experiment, the researchers used many compounds, for example, 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate (cas: 219543-09-6COA of Formula: C11H21BF4N2O2).
4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate (cas: 219543-09-6) belongs to piperidine derivatives. The piperidine structural motif is present in numerous natural alkaloids. These include piperine, which gives black pepper its spicy taste. Some chemotherapeutic agents have piperidine moiety within their structure, foremost among them, vinblastine and raloxifene.COA of Formula: C11H21BF4N2O2
Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem