Synthesis of allyl chlorides

Recent Literature

AcCl-EtOH transforms primary and secondary allyl acetates into allyl chlorides that retain the olefinic bond in the more stable position. Secondary allyl alcohols react with almost the same efficacy as the acetates, but the reactions of primary allyl alcohols that possess 1,2-disubstituted alkenes are very slow. Simple removal of the volatiles gives products in high purity.
V. K. Yadav, K. G. Babu, Tetrahedron, 2003, 59, 9111-9116.

V. K. Yadav, K. G. Babu, Tetrahedron, 2003, 59, 9111-9116.

Aryl allylic alcohols are converted to halogenated unsaturated ketones or allylic halides under Moffatt-Swern Conditions using excess DMSO and oxalyl chloride or oxalyl bromide. Electron-poor aromatic rings favor formation of the halogenated ketone, while electron-donating substituents in the ortho or para positions favor formation of the allylic halide.
J. Yin, C. E. Gallis, J. D. Chisholm, J. Org. Chem., 2007, 72, 7054-7057.

Activating of magnesium alkoxides using TiCl₄ allows the generation of allylic chlorides. An efficient, one-pot method for the conversion of carbonyl electrophiles to allylic chlorides has been developed.
M. J. Fuchter, J.-N. Levy, Org. Lett., 2008, 10, 4919-4922.

M. J. Fuchter, J.-N. Levy, Org. Lett., 2008, 10, 4919-4922.