2,2,6,6-Tetramethylpiperidin-1-yloxycarbonyl: A Protecting Group for Primary, Secondary, and Heterocyclic Amines

Joseph R Lizza1, Maximilian Bremerich2, Stephanie R McCabe1

  • 1Department of Chemistry , University of Pittsburgh , Pittsburgh , Pennsylvania 15260 , United States.

Organic Letters
|October 24, 2018
PubMed

Related Concept Videos

Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).
7.0K
Nomenclature of Aryl and Heterocyclic Amines01:10

Nomenclature of Aryl and Heterocyclic Amines

The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.
3.2K
Primary and Secondary Growth in Roots and Shoots03:02

Primary and Secondary Growth in Roots and Shoots

Vascular plants, which account for over 90% of the Earth’s vegetation, all undergo primary growth—which lengthens roots and shoots. Many land plants, notably woody plants, also undergo secondary growth—which thickens roots and shoots.
60.5K
Nomenclature of Secondary and Tertiary Amines01:12

Nomenclature of Secondary and Tertiary Amines

The secondary and tertiary amines are derivatives of ammonia, where two and three of its hydrogens are replaced by alkyl groups, respectively. Secondary and tertiary amines can be symmetrical with identical alkyl groups attached to the nitrogen atom or unsymmetrical when more than one type of alkyl group is present. The standard nomenclature of secondary and tertiary amines is similar to the names given to the primary amines. They are generally named alkylamines. As depicted in Figure 1, for...
5.2K
Primary and Secondary Reinforcers01:23

Primary and Secondary Reinforcers

In psychology, reinforcement is a key concept in behavior modification. B.F. Skinner demonstrated this with his experiments involving rats in what is known as a Skinner box. The rats learned to press a lever to receive food, a primary reinforcer that fulfilled their innate need for nourishment.
Effective reinforcers for humans vary depending on the individual and the context. Primary reinforcers, such as food, water, sleep, shelter, and pleasure, have inherent value and satisfy basic biological...
1.0K
Nomenclature of Primary Amines01:17

Nomenclature of Primary Amines

Primary, secondary, and tertiary amines are compounds consisting of one, two, and three alkyl groups connected to the amino group (–NH2), respectively. As depicted in Figure 1, the common name of the primary amines is obtained by adding the suffix -amine to the alkyl substituent attached to the amino group as the corresponding alkylamine.
4.5K