THE 2,4,6-TRINITROBENZYL ANION AS A NUCLEOPHILIC REAGENT WITH ARYL HALIDES. PREPARATION OF POLYNITRODIPHENYLMETHANES,
Abstract
2,2',4,4',6,6'-Hexanitrodiphenylmethane has been prepared by the nucleophilic attack of the 2,4,6-trinitrobenzyl anion on picryl chloride in tetrahydrofuran-dimethysulfoxide solutions. Similarly, a series of polynitrodiphenylmethanes has been prepared by using other halonitrobenzenes as substrates in the reaction with the trinitrobenzyl anion. Since there is a competitive reaction of the trinitrobenzyl anion with unionized trinitrotoluene to form 2,2',4,4',6,6'-hexanitrobibenzyl, only those halonitrobenzenes in which the halogen is sufficiently labile to react at a rate faster than the trinitrotoluene bimolecular reaction rate form the nitrodiphenylmethanes. The results obtained are consistent with the data reported in the literature for the reactivity ordering of polynitrohalobenzenes with other nucleophiles. (Author)
Document Details
- Document Type
- Technical Report
- Publication Date
- Jun 02, 1967
- Accession Number
- AD0382303
Entities
People
- Kathryn G. Shipp
- Lloyd A. Kaplan
Organizations
- Naval Ordnance Laboratory