Cyclopropanecarboxaldehyde reacts with Grignard or organolithium reagents to give the expected secondary alcohols. These are susceptible to ring opening in the presence of HBr, providing stereoselective access to homoallylic bromides. It is also used in the synthesis of eta(2)-enonenickel complexes by reacting with [Ni(cod)(2)] (cod = 1,5-cyclooctadiene) and PBu(3) and to prepare a cyclopropylidene tetralone which underwent an enantioselective palladium-catalyzed [3+2] TMM cycloaddition providing a chiral spiro-fused cyclopentene.
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Applications
Cyclopropanecarboxaldehyde reacts with Grignard or organolithium reagents to give the expected secondary alcohols. These are susceptible to ring opening in the presence of HBr, providing stereoselective access to homoallylic bromides. It is also used in the synthesis of eta(2)-enonenickel complexes by reacting with [Ni(cod)(2)] (cod = 1,5-cyclooctadiene) and PBu(3) and to prepare a cyclopropylidene tetralone which underwent an enantioselective palladium-catalyzed [3+2] TMM cycloaddition providing a chiral spiro-fused cyclopentene.
Solubility
Soluble in water.
Notes
Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage. Recommended storage temperature is 2 - 8°C. It is sensitive to air.
RUO – Research Use Only
General References:
- Lewis Brewster Young.; Walter S. Trahanovsky. Cerium(IV) oxidation of organic compounds. III. Preparation of cyclopropanecarboxaldehyde from cyclopropanemethanol. J. Org. Chem. 1967, 32 (7), 2349-2350.
- J. R. Durig.; Fusheng Feng.; T. S. Little.; Ai -Ying Wang. Conformational stability, barriers to internal rotation, structural parameters, ab initio calculations, and vibrational assignment of cyclopropanecarboxaldehyde. Structural Chemistry. 1992, 3 (6), 417-428.
- Reacts with Grignard or organolithium reagents to give the expected secondary alcohols. These are susceptible to ring opening in the presence of HBr, providing stereoselective access to homoallylic bromides: Synth. Commun., 25, 3351 (1995):