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Allyl chloride is used as an alkylating agent. It is used in treatment with sodium bis(trimethylsilyl)amide gives the strained, highly reactive alkene cyclopropene.
Kenji Uneyama.; Nobuyoshi Kamaki.; Akihiko Moriya.; Sigeru Torii. Tin(II)-aluminum-promoted allylation of aldehydes with allyl chloride in an aqueous solvent system. J. Org. Chem. 1985, 50 (25), 5396-5399.
Farley Fisher.; Douglas E. Applequist. Synthesis of 1-Methylcyclopropene. J. Org. Chem. 1965, 30 (6), 2089-2090.
Lithiation with LDA in THF at -78o generatesɑ-chloroallyllithium which can be ɑ-alkylated with primary bromides in high yield. Displacement of the resulting allylic chloride with a dialkyl cuprate to give, stereoselectively, an (E)-alkene, has been used in a pheromone synthesis: J. Org. Chem., 45, 1504 (1981).
Treatment with sodium bis(trimethylsilyl)amide gives the strained, highly reactive alkene cyclopropene. For details and Diels-Alder reactions, see: J. Org. Chem., 61, 6462 (1996).
Hazard Statements: H225-H302-H312-H332-H315-H319-H341-H351-H335-H373
Highly flammable liquid and vapour. Harmful if swallowed. Harmful in contact with skin. Harmful if inhaled. Causes skin irritation. Causes serious eye irritation. Suspected of causing genetic defects. Suspected of causing cancer. May cause respiratory irritation. May cause damage to organs through prolonged or repeated exposure.
Precautionary Statements: P210-P260-P303+P361+P353-P305+P351+P338-P405-P501a
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Do not breathe dust/fume/gas/mist/vapours/spray. 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.