Allylic Rearrangements

L. Claisen, Ber. 45, 3157 (1912).

Migration of a carbon-carbon double bond in a three carbon (allylic) system on treatment with nucleophiles under SN1 conditions (or under SN2 conditions when the nucleophilic attack takes place at the γ-carbon):



Reviews: J. R. DeWolfe, W. G. Young, Chem. Rev. 56, 753 (1956); W. G. Young, J. Chem. Ed. 39, 455 (1962); P. de la Mare in Molecular Rearrangements Part 1, P. de Mayo, Ed. (Wiley-Interscience, New York, 1963) pp 27-110; K. Mackenzie in The Chemistry of Alkenes, S. Patai, Ed. (Interscience, New York, 1964) pp 436-453; R. H. DeWolfe, W. G. Young in ibid. pp 681-738; J. March, Advanced Organic Chemistry (Wiley-Interscience, New York, 4th ed., 1992) pp 327-330.