The Control of Isomer Distributions in Nitration Reactions.
Abstract
The direct metalation of benzene and its derivatives by mercury(II), thallium(III), lead(IV), and palladium(II) has been investigated. Mercury(II) and palladium(II) catalyze the nitration of toluene and other aromatic compounds. A novel isomer distribution is realized because the metallation reaction is the rate-controlling and product-controlling step. The nitration of toluene via thallation-nitrosode thallation produces a more random product distribution in a non-catalytic reaction. The plumbylation of toluene is an unusually selective reaction. The aryllead(IV) com pounds can be cleaved by a variety of reagents to form carbon-halogen, carbon-nitrogen, carbon-sulfur, and carbon-carbon bonds. This research has established that the nitronium ion carrier approach is not a fruitful one for the alteration of product distributions in nitration reactions. It seems doubtful that isomer distributions can be, in general, controlled by tactics of this kind. On the other hand, this research work indicates that the metal mediated electrophilic substitution reactions offer an effective approach for the control of isomer distributions. More work is needed in this area to exploit this method for catalysis and the simultaneous control of isomer distributions in a variety of substitution reactions.
Document Details
- Document Type
- Technical Report
- Publication Date
- Jun 10, 1980
- Accession Number
- ADA086286
Entities
People
- Leon M. Stock
Organizations
- University of Chicago