Preparation of the Optical Isomers of Soman
Abstract
Pinacolyl alcohol was resolved into its enantiomers, which were reacted with methyldicholorophoshine in such a way as to produce the corresponding O-pinacolyl methylphosphonothioic acids. These acids were resolved at phosphorus using the two enantiomers of alpha-phenethylamine. Approximately 10 grams of the following four compounds were prepared: the (-)-alpha-phenethylamine salt of C(+)P(-)- and C(-)P(-)-O-pinacolyl methylphonothioic acid and the (+)-alpha-phenethylamine salt of C(+)P(+)- and C(-)P(+)-O-pinacolyl methylphosphonothioic acid. As a model for the preparation of all the optical isomers of soman, both the (+)-alpha-phenethylamine salt and the sodium salt of C(+)P(+)-O-pinacolyl methylphosphonothioic acid were reacted with picryl fluoride in the presence and absence of alumina, which is postulated to be a fluoride-trapping agent. The best results were obtained using the sodium salt in the presence of alumina. In this case, the sodium salt of C(+)O(+)-O-pinacolyl methylphosphonothioic acid was converted in essentially quantitative yield to a mixture consisting of 76% C(+)P(-)-soman contaminated with 24% C(+)P(+)-soman. It is conceivable that the isomers of soman could be prepared in even greater optical purity and that this approach could lead to a method for the preparation of milligram to gram quantities of all four of the optical isomers of soman.
Document Details
- Document Type
- Technical Report
- Publication Date
- Feb 01, 1985
- Accession Number
- ADA179265
Entities
People
- Allison F. Jr Fentiman
Organizations
- Battelle Memorial Institute