29770-78-3

Basic information

• Product Name: 3-(4-chlorophenyl)-2-oxa-3-azabicyclo[2.2.2]oct-5-ene
• Synonyms: 3-(4-chlorophenyl)-2-oxa-3-azabicyclo[2.2.2]oct-5-ene
• CAS NO: 29770-78-3
• Molecular Weight: 221.686
• Mol File: 29770-78-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 3-(4-chlorophenyl)-2-oxa-3-azabicyclo[2.2.2]oct-5-ene(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-chlorophenyl)-2-oxa-3-azabicyclo[2.2.2]oct-5-ene(29770-78-3)
• EPA Substance Registry System: 3-(4-chlorophenyl)-2-oxa-3-azabicyclo[2.2.2]oct-5-ene(29770-78-3)

Safety Data

• Hazardous Substances Data: 29770-78-3(Hazardous Substances Data)

Upstream product

• 106-47-8 4-chloro-aniline 
• 1165952-91-9 cyclohexa-1,3-diene 
• 932-98-9 1-chloro-4-nitroso-benzene 

Downstream Products

• 29738-38-3 3-(4-chloro-phenyl)-2-oxa-3-aza-bicyclo[2.2.2]octane-5exo,6exo-diol 

Relevant articles and documents

A molybdenum-catalyzed oxidative system forming oxazines (hetero-Diels-Alder adducts) from primary aromatic amines, hydrogen peroxide, and conjugated dienes

The development of a new molybdenum-catalyzed procedure for the formation of oxazines-hetero-Diels-Alder adducts - from primary aromatic amines, hydrogen peroxide, and conjugated dienes is presented. The method is based on a molybdenum-peroxo complex, which in the presence of hydrogen peroxide as the terminal oxidant selectively catalyzes the oxidation of primary aromatic amines to the corresponding dienophilic nitroso compounds. The molybdenum-peroxo catalyst is under the present reaction conditions not reactive toward conjugated dienes and substituents attached to the aromatic nuclei of the primary aromatic amines. Several oxazines are synthezised following this new procedure using primary aromatic amines having either electron-withdrawing or electron-donating substituents and 1,3-cyclohexadiene as the standard diene. The scope of the new procedure is also demonstrated by the preparation of several oxazines using different alkyland phenyl-substituted conjugated dienes and 4-chloroaniline as precursor for the dienophile. Moderate diastereomeric excesses are found when the reaction is carried out with 1-(2-aminophenyl)-ethanol and 1,3-cyclohexadiene or (E)-1-phenyl-1,3-butadiene. The stereochemical and electronic factors governing the reaction course are briefly discussed.

In situ generation of nitroso compounds from catalytic hydrogen peroxide oxidation of primary aromatic amines and their one-pot use in hetero-Diels-Alder reactions

A method for in situ generation of nitroso compounds from organoselenium-catalyzed oxidation of anilines by hydrogen peroxide was developed. The generated nitroso compounds were subsequently used in hetero-Diels-Alder reactions. A variety of oxazines were synthesized in reasonable to good yields by this one-pot procedure using primary aromatic amines with different substituents and various conjugated dienes. This strategy might facilitate the current methodologies for nitroso chemistry since no isolation or purification of the nitroso compounds is required. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.