Level 3 – Case 35
236
In Summary
Owing to the superb leaving group ability of the iodonio group, vinyl iododium
salts give different products under solvolysis conditions. Depending on the structure of the salt, in-plane vinylic S N 2 substitution, nucleophilic substitution with
neighboring group participation, and even elimination processes can be observed.
Additional Comments
This problem is based on the work by Okuyama T, Ochiai M (1997) J. Am. Chem.
Soc. 119:4785-4786 and by Gronheid R, Lodder G, Okuyama T (2002) J. Org.
Chem. 67:693-702.
Subjects of Revision
Solvolysis. S N 2 and D-elimination reactions. Neighboring group participation. Nucleophilicity and basicity. Carbocations: stability.
236
In Summary
Owing to the superb leaving group ability of the iodonio group, vinyl iododium
salts give different products under solvolysis conditions. Depending on the structure of the salt, in-plane vinylic S N 2 substitution, nucleophilic substitution with
neighboring group participation, and even elimination processes can be observed.
Additional Comments
This problem is based on the work by Okuyama T, Ochiai M (1997) J. Am. Chem.
Soc. 119:4785-4786 and by Gronheid R, Lodder G, Okuyama T (2002) J. Org.
Chem. 67:693-702.
Subjects of Revision
Solvolysis. S N 2 and D-elimination reactions. Neighboring group participation. Nucleophilicity and basicity. Carbocations: stability.