REACTION OF THE TRITYL CATION WITH DIMETHYLKETENE DIMETHYLACETAL,
Abstract
The reaction of trityl bromide with dimethylketene dimethylacetal yields a quinoidal ester derivative, resulting from reaction of the trityl cation at a para position. Treatment of this ester with methanolic sodium methoxide converts it to an aromatized isomer. The formation of the quinoidal ester makes it clear that the trityl ion reacts at a para position with dimethylketene acetal as a relatively highly hindered nucleophile to give a quinoidal cation which then leads to the quinoidal ester. The results emphasize the possibility of reactions of the trityl cation with nucleophiles at a benzene ring position, giving rise to new final products or possible transient intermediates with the nucleophile at a ring position instead of the central carbon atom. (Extracted)
Document Details
- Document Type
- Technical Report
- Publication Date
- Jun 08, 1964
- Accession Number
- AD0612670
Entities
People
- Phillip S. Magee
- Richard Heck
- S. Winstein
Organizations
- University of California, Los Angeles