Rearrangements in Vinyl Cations

The literature data on the rearrangements of vinyl cationoid intermediates arising in the solvolysis of various vinyl derivatives and in the addition of cationoid reagents to the triple bond are examined and the differences between the rearrangements of vinyl cations and those of the "usual" saturated carbonium ions are demonstrated. The influence of the structure of vinyl cationoid intermediates on the rate and mode of rearrangements of various types (the migration of alkyl and aryl groups, shifts via the double bond and to a double bond, and higher-order shifts) are discussed.
The bibliography includes 87 references.