73308-42-6

Basic information

• Product Name: N-benzyl-N-phenyl-2-phenylacetamide
• Synonyms: N-benzyl-N-phenyl-2-phenylacetamide
• CAS NO: 73308-42-6
• Molecular Weight: 301.388
• Mol File: 73308-42-6.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: N-benzyl-N-phenyl-2-phenylacetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-benzyl-N-phenyl-2-phenylacetamide(73308-42-6)
• EPA Substance Registry System: N-benzyl-N-phenyl-2-phenylacetamide(73308-42-6)

Safety Data

• Hazardous Substances Data: 73308-42-6(Hazardous Substances Data)

Upstream product

• 103-82-2 phenylacetic acid 
• 758640-21-0 N-Benzylaniline 
• 7477-20-5 (3S,4R)-1,3,4-triphenyl-2-azetidinone 
• 7477-20-5 (±)-cis-1,3,4-triphenylazetidin-2-one 
• 16141-49-4 trans-1,3,4-triphenyl-2-azetidinone 
• 621-06-7 2,N-diphenylacetamide 
• 100-44-7 benzyl chloride 
• 18101-13-8 2,3,5-triphenyl-thiazolidin-4-one 

Relevant articles and documents

Metal-Free Formal Oxidative C?C Coupling by In Situ Generation of an Enolonium Species

Much contemporary organic synthesis relies on transformations that are driven by the intrinsic, so-called “natural”, polarity of chemical bonds and reactive centers. The design of unconventionally polarized synthons is a highly desirable strategy, as it generally enables unprecedented retrosynthetic disconnections for the synthesis of complex substances. Whereas the umpolung of carbonyl centers is a well-known strategy, polarity reversal at the α-position of a carbonyl group is much rarer. Herein, we report the design of a novel electrophilic enolonium species and its application in efficient and chemoselective, metal-free oxidative C?C coupling.

Ring splitting of azetidin-2-ones via radical anions

The radical anions of azetidin-2-ones, generated by UV-irradiation in the presence of triethylamine, undergo ring-splitting via N-C4 or C3-C4 bond breaking, leading to open-chain amides. This reactivity diverges from that found for the neutral excited states, which is characterised by α-cleavage. The preference for β-cleavage is supported by DFT theoretical calculations on the energy barriers associated with the involved transition states. Thus, injection of one electron into the azetidin-2-one moiety constitutes a complementary activation strategy which may be exploited to produce new chemistry.

Reaction of Mesoionic Thiazolones with m-Chloroperbenzoic Acid. Oxidative Dipole Extensions

The oxidation of anhydro-4-hydroxy-2,3,5-triarylthiazolium hydroxides (1) with m-chloroperbenzoic acid gave (in primary alcohols) 2,5-dialkoxy-2,3,5-triarylthiazolidin-4-ones (5) and N-aroylthiobenzanilides (6).Oxidation of anhydro-5-hydroxy-3-methyl-2-phenylthiazolium hydroxide (2) gave 3-methyl-2-phenylthiazolidine-4,5-dione (8) and N-formyl-N-methylthiobenzamide (9).The products arise from initial oxidations at the carbon atoms at position 5 of 1 and position 4 of 2, and transformation modes to the final products are discussed.These oxidations are the first examples of oxidative dipole extensions.