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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.
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):
Dichiarazioni di rischio (UE): H225-H314-H318
Highly flammable liquid and vapour. Causes severe skin burns and eye damage. Causes serious eye damage.
Dichiarazioni precauzionali: P210-P260u-P303+P361+P353-P305+P351+P338-P405-P501a
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Do not breathe dusts or mists. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.