87768-58-9

Basic information

• Product Name: N-isopropyl-o-deuteriobenzamide
• Synonyms: N-isopropyl-o-deuteriobenzamide
• CAS NO: 87768-58-9
• Molecular Weight: 164.211
• Mol File: 87768-58-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: N-isopropyl-o-deuteriobenzamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-isopropyl-o-deuteriobenzamide(87768-58-9)
• EPA Substance Registry System: N-isopropyl-o-deuteriobenzamide(87768-58-9)

Safety Data

• Hazardous Substances Data: 87768-58-9(Hazardous Substances Data)

Upstream product

• 5440-69-7 N-isopropylbenzamide 
• 20383-28-2 N,N-diisopropyl benzamide 

Relevant articles and documents

Complex-induced proximity effects in directed lithiations: Analysis of intra- and intermolecular kinetic isotope effects in directed aryl and benzylic lithiations

The mechanism of proton transfers in directed lithiations has been investigated by measuring the intra- and intermolecular kinetic isotope effects for the benzylic lithiation of N-benzyl-N,N′-dimethyl urea (6) and the ortho lithiations of the tertiary ami

A COMPARISON OF SECONDARY AND TERTIARY AMIDES AS DIRECTORS OF ORTHO AND ADJACENT BENZYLIC LITHIATION AND OF ASYMMETRIC INDUCTION IN ORTHO LITHIATED BENZAMIDES

Comparisons are made between the influence of secondary and tertiary amides on ortho and adjacent benzylic metallations of benzamides.In the intramolecular competition offered by N,N-diethyl-N-ethylterephthalamide (1) the tertiary amide is the more effective director of ortho lithiation, while the secondary amide is better in the intermolecular competitions offered by the pairs N-ethyl-(9):N,N-diethylbenzamide(10) and N-isopropyl-(11):N,N-diisopropylbenzamide(12).Both secondary and tertiary amides are found to direct metallation ortho to the amide in the 2-isopropylbenzamides 25 and 26; however, benzylic metallation is observed with secondary 2-ethyl- and 2-methylbenzamides 21 and 22 and with the tertiary 2-ethylbenzamide 19.Magnetic non-equivalence is noted for the anti-N-methylene group of 19.The reaction of an ortho lithio (S)-O-methyl-N-benzoylleucinol (34) with 1-naphthaldehyde-1-d gives, after lactonization, 3-(1-naphthyl-1-d)-phthalide with 10percent enantiomeric excess.The phthalide can be obtained in high enantiomeric purity by separation of the diastereoisomers prior to cyclization.Control experiments establish that the observed asymmetric induction is attributable to diastereomeric transition states.The corresponding tertiary benzamide is ineffective in inducing asymmetry.Structural and mechanistic rationales are offered for these observations.