20396-49-0

Basic information

• Product Name: Cyclohexanecarboperoxoic acid, 1,1-dimethylethyl ester
• CAS NO: 20396-49-0
• Molecular Formula: C11H20O3
• Molecular Weight: 200.278
• Mol File: 20396-49-0.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: Cyclohexanecarboperoxoic acid, 1,1-dimethylethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexanecarboperoxoic acid, 1,1-dimethylethyl ester(20396-49-0)
• EPA Substance Registry System: Cyclohexanecarboperoxoic acid, 1,1-dimethylethyl ester(20396-49-0)

Safety Data

• Hazardous Substances Data: 20396-49-0(Hazardous Substances Data)

Upstream product

• 75-91-2 tert.-butylhydroperoxide 
• 98-89-5 Cyclohexanecarboxylic acid 
• 2043-61-0 cyclohexanecarbaldehyde 
• 2719-27-9 cyclohexanylcarbonyl chloride 

Downstream Products

• 79650-21-8 α-cyclohexyl-p-methylacetophenone 
• 18869-27-7 (E)-(2-cyclohexylvinyl)benzene 
• 40115-03-5 2-cyclohexyl-benzothiazole 
• 89482-40-6 2-cyclohexyloxy-1,1,3,3-tetramethyl-2,3-dihydro-1H-isoindole 
• 3141-58-0 tert-butoxy radical 
• 3198-23-0 cyclohexane carboxylate 
• 192189-54-1 cis-4-phthaloylaminocyclohexanecarboxylic acid methyl ester 
• 619-50-1 4-nitrobenzoic acid methyl ester 
• 105-07-7 4-cyanobenzaldehyde 

Relevant articles and documents

FeCl2-Catalyzed Decarboxylative Radical Alkylation/Cyclization of Cinnamamides: Access to Dihydroquinolinone and Pyrrolo[1,2- a]indole Analogues

A simple and unified method for the synthesis of alkylated dihydroquinolinone and pyrrolo[1,2-a]indole derivatives in moderate to high yields (up to 91%) with excellent diastereoselectivity (>20:1 dr) was developed. The inexpensive FeCl2·4H2O works as catalyst, and easily prepared peresters (or peroxides) from aliphatic acids act as alkylating reagents and single electron oxidants. This environmentally friendly reaction proceeds via an FeCl2-catalyzed alkyl radical cascade addition/cyclization fashion.

Iron-Catalyzed Vinylic C?H Alkylation with Alkyl Peroxides

A variety of alkyl peresters and alkyl diacyl peroxides, which are readily accessible from carboxylic acids, are utilized as general primary, secondary, and tertiary alkylating reagents for iron-catalyzed vinylic C?H alkylation of vinyl arenes, dienes, and 1,3-enynes. This transformation affords olefinic products in up to 98 % yield with high E/Z values. A broad range of functionalities, including carboxyl, boronic acid, methoxy, ester, amino, and halides, are tolerated. This protocol provides a facile approach to some olefins that are difficult to access, and hence, offers an alternative to existing systems. The synthetic utility of this method is demonstrated by late-stage functionalization of selected natural-product derivatives.

Iron-Catalyzed Radical Decarboxylative Oxyalkylation of Terminal Alkynes with Alkyl Peroxides

An iron-catalyzed oxyalkylation of alkynes with alkyl peroxides as the alkylating reagents has been investigated. Alkyl peroxides are readily available from aliphatic acids and serve simultaneously as the alkylating reagents and internal oxidants. Primary, secondary, and tertiary alkyl groups of aliphatic acids were readily incorporated into C?C triple bonds and diverse α-alkylated ketones were synthesized. Mechanism studies revealed that this reaction involves highly reactive alkyl free radicals. A unique equilibrium between lauric acid and water catalyzed by the iron(III) catalyst was observed.