imidotriphenylphosphorus

• CAS: 2240-47-3
• Catalog Number: ACM2240473
• Category: Main Products
• Molecular Weight: 275.28
• Molecular Formula: C18H14NP
• Synonyms: Triphenylphosphine imide
• Appearance: White solid

Case Study

Triphenylphosphine Imide as a Key Reagent for the Synthesis of Methyl α-Iminotrifluoropropionate

Rassukana, Yuliya V. Synthesis 2011.21 (2011): 3426-3428.

α-Iminocarboxylates bearing a trifluoromethyl group are valuable building blocks for constructing biologically active amino acid derivatives and heterocycles. In this study, triphenylphosphine imide (Ph3P=NH) was employed as a nitrogen-transfer reagent in an aza-Wittig reaction with methyl trifluoropyruvate to synthesize the first example of methyl α-iminotrifluoropropionate.
The reaction proceeds via nucleophilic addition of triphenylphosphine imide across the highly electrophilic carbonyl group of methyl trifluoropyruvate, forming a stable phosphine imide adduct. Upon heating or distillation, this intermediate undergoes 1,3-proton transfer and elimination of triphenylphosphine oxide, cleanly affording the target N-H imine in 80% yield. The product exists as an equilibrium mixture of E/Z isomers (10:1 ratio at 25 °C) and serves as a versatile synthon for trifluoroalanine derivatives.
Key Results:
· Triphenylphosphine imide enables direct access to methyl α-iminotrifluoropropionate (3) via a two-step aza-Wittig sequence, overcoming the instability of the free N-H imine.
· The imine reacts with indole to give methyl 2-amino-3,3,3-trifluoro-2-(1H-indol-3-yl)propanoate (4) in 90% yield, demonstrating nucleophilic addition at the polarized C=N bond.
· Cyclocondensation with mercaptoacetic acid, 3-mercaptopropionic acid, or thiosalicylic acid affords thiazolidinone 5 (92%), thiazinanone 6 (92%), and benzothiazine 7 (95%), respectively-heterocycles incorporating the trifluoroalanine residue.
· [3+2] Dipolar cycloaddition with nitrile oxide gives dihydro-1,2,4-oxadiazole 8 (90%), while reaction with salicylaldehyde yields 2H-1,3-benzoxazine 9 (60%) via O-H addition and intramolecular condensation.
· The free N-H function allows electrophilic functionalization: reaction with methyl trifluoropyruvate affords the highly functionalized imine 10 quantitatively.

Custom Q&A

What is the molecular formula of Imidotriphenylphosphorus?

The molecular formula of Imidotriphenylphosphorus is C18H16NP.

When was Imidotriphenylphosphorus first created?

Imidotriphenylphosphorus was first created on March 26, 2005.

What is the molecular weight of Imidotriphenylphosphorus?

The molecular weight of Imidotriphenylphosphorus is 277.3 g/mol.

What is the InChIKey of Imidotriphenylphosphorus?

The InChIKey of Imidotriphenylphosphorus is DHOUOTPZYIKUDF-UHFFFAOYSA-N.

How many hydrogen bond donor counts does Imidotriphenylphosphorus have?

Imidotriphenylphosphorus has 1 hydrogen bond donor count.

What is the topological polar surface area of Imidotriphenylphosphorus?

The topological polar surface area of Imidotriphenylphosphorus is 23.8Ų.

Does Imidotriphenylphosphorus have any isotope atom count?

No, Imidotriphenylphosphorus does not have any isotope atom count.

What is the exact mass of Imidotriphenylphosphorus?

The exact mass of Imidotriphenylphosphorus is 277.102036512 g/mol.

How many defined bond stereocenter counts does Imidotriphenylphosphorus have?

Imidotriphenylphosphorus has 0 defined bond stereocenter count.

Is the compound of Imidotriphenylphosphorus canonicalized?

Yes, the compound of Imidotriphenylphosphorus is canonicalized.