(1-Ethoxycarbonylcyclopropyl)triphenylphosphonium tetrafluoroborate

• Catalog No.: A18305
• CAS Number: 52186-89-7
• M. F.: C24H24BF4O2P
• M. W.: 462.2245338
• Purity: 98%

SYNONYMS

• Title: (1-乙氧基羰基环丙基)三苯基磷四氟硼酸盐
• IUPAC name: [1-(ethoxycarbonyl)cyclopropyl]triphenylphosphanium; tetrafluoroboranuide
• IUPAC Traditional name: [1-(ethoxycarbonyl)cyclopropyl]triphenylphosphanium tetrafluoroborate
• Synonyms: (1-Carboethoxycyclopropyl)triphenylphosphonium tetrafluoroborate; Fuchs' Reagent

DATABASE IDS

• CAS Number: 52186-89-7
• Beilstein Number: 4650673
• MDL Number: MFCD00051879

PROPERTIES

• Purity: 98%
• Melting Point: 173-179°C
• GHS Hazard statements: H315-H319-H335
• European Hazard Symbols: Irritant (Xi)
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: 否

REFERENCES

• Cyclic imides e.g. Succinimide, A13503, give bridgehead lactams: Liebigs Ann. Chem., 521 (1983); for reaction scheme, see Glutarimide, L00968.
• Valuable intermediate for cycloalkenylation of compounds containing a nucleophilic center and a carbonyl group. Nucleophilic ring-opening of the cyclopropyl ring is followed by intramolecular Wittig reaction (see Appendix 1) of the intermediate carbonyl-phosphorane; e.g., with ?-keto esters, cyclopentenes are formed: J. Am. Chem. Soc., 96, 1607 (1974):
  
• With 2-formylcyclohexanones, spirocyclopentenes are obtained: J. Am. Chem. Soc., 99, 7307 (1977). Na carboxylates give 2,3-dihydrofurans: Tetrahedron Lett., 4353 (1975), and thiolcarboxylates give dihydrothiophenes, readily aromatized to thiophenes with DDQ: J. Chem. Soc., Perkin 1, 2403 (1994):