15567-46-1

Upstream product

• 1119-57-9 N-methyloctanoylamide 
• 111-64-8 n-octanoic acid chloride 

Downstream Products

• 20299-80-3 1-(pyrrolidin-1-yl)octan-1-one 
• 70659-87-9 N-benzyloctanoic amide 

Relevant academic research and scientific papers

Supramolecular fixation of NO2 with calix[4]arenes

Reaction of NO2 with simple calix[4]arenes in chloroform in the presence of a Lewis acid rapidly results in intense coloration caused by the encapsulation of nitrosonium cation.

Sensing and fixation of NO2/N2O4 by calix[4]arenes

An approach toward visual detection and chemical utilization of NO2/N2O4 is proposed, which employs simple calix[4]arenes. Exposure of tetra-O-alkylated calix[4]arenes 1 and 2, possessing either a cone or a 1,3-alternate conformation, to NO2/N2O4, both in chloroform solution and in the solid state, results in deeply colored calixarene-nitrosonium (NO+) complexes. In the presence of a Lewis acid, such as SnCl4, stable calixarene-NO+ complexes 7 and 8 were isolated in a quantitative yield and characterized by UV-vis, FTIR, high-resolution 1H NMR spectroscopy and elemental analysis. NO+ is found encapsulated within the calixarene cavity, and stable charge-transfer complexes result with Kass > 106 M-1 (CDCl3). The NO+ encapsulation was also demonstrated in titration experiments with calixarenes 1, 2, and 5 and commercially available NO+SbF6- salt in chloroform. The complexation process is reversible, and the complexes dissociate upon addition of water and alcohol, recovering the parent calixarenes. Attachment of functionalized calix[4]arenes to silica gel was demonstrated, which afforded a solid material 15 capable of visual detection and entrapment of NO2/N2O4. Calixarene-NO+ complexes can be utilized for the NO+ transfer processes and nitrosation reactions. The NO+ guest transfer between two calixarene containers 2 and 5 was achieved and studied by UV-vis and 1H NMR spectroscopy. Chemical fixation of NO2/N2O4 was demonstrated through their quantitative transformation into the calixarene-NO+ complex and its use as a nitrosonium transfer agent in the synthesis of N-nitrosoamides. These results may lead toward novel nitrogen oxides storing materials.

Polymer-supported calix[4]arenes for sensing and conversion of NO 2/N2O4

The use of simple calix[4]arenes 1a,b for NO2/N 2O4 sensing and conversion is demonstrated, both in solution and in the solid state. Upon reacting with these gases, compounds 1a,b encapsulate reactive NO+ cation

Tert -Butyl nitrite promoted transamidation of secondary amides under metal and catalyst free conditions

A mild and efficient method is demonstrated for the transamidation of secondary amides with various amines including primary, secondary, cyclic and acyclic amines in the presence of tert-butyl nitrite. The reaction proceeds through the N-nitrosamide intermediate and provides the transamidation products in good to excellent yields at room temperature. Moreover, the developed methodology does not require any catalyst or additives.

Towards supramolecular fixation of NOx gases: Encapsulated reagents for nitrosation

The use of simple calix[4]arenes for chemical conversion of NO2/ N2O4 gases is demonstrated in solution and in the solid state. Upon reacting with these gases, calixarenes 1 encapsulate nitrosonium (NO+) cations within their cavities with the formation of stable calixarene-NO+ complexes 2. These complexes act as encapsulated nitrosating reagents; cavity effects control their reactivity and selectivity. Complexes 2 were effectively used for nitrosation of secondary amides 5, including chiral derivatives. Unique size-shape selectivity was observed, allowing for exclusive nitrosation of less crowded N-Me amides 5a-e (up to 95% yields). Bulkier N-Alk (Alk > Me) substrates 5 did not react due to the hindered approach to the encapsulated NO+ reagents. Robust, silica gel based calixarene material 3 was prepared, which reversibly traps NO 2/ N2O4 with the formation of NO +-storing silica gel 4. With material 4, similar size-shape selectivity was observed for nitrosation. The N-Me-N-nitroso derivatives 6d,e were obtained with ～30% yields, while bulkier amides were nitrosated with much lower yields (+ species, which can be generated by a number of NOx gases, these supramolecular reagents and materials may be useful for NOx entrapment and separation in the environment and biomedical areas.

Toward Synthetic Tubes for NO2/N2O4: Design, Synthesis, and Host-Guest Chemistry

Design of molecular nanotubes is proposed for entrapment and conversion of NO2/N2O4 gases. Synthesis of 1,3-alternate bis-calix[4]arene tube 3 of 5 × 11 A internal dimensions is presented, and its reversible reactions with

Encapsulated reagents for nitrosation

(Matrix presented) A novel class of stable, mild, and size-shape-selective nitrosating agents for secondary amides is introduced. These are based on reversible entrapment and release of reactive nitrosonium species by calix[4]arenes. The NO+ encapsulation controls the reaction selectivity.