Preparation and properties of N-pentafluorosulfanylamido derivatives

N,N’-Bis (pentafluorosulfanyl )urea was synthesized from. thiazyl trifluoride, carbonyl fluoride, and either anhydrous hydrogen chloride. Attempts at reacting the urea with ethyl malonate, malonic acid, malonyl chloride, carbon suboxide, and ethyl crotonate all failed. The urea was found to be unstable in both acidic and basic media. N,N’-Bis(pentafluorosulfanyl)malonamide was prepared from pentafluorosulfanylamine and carbon suboxide by mixing them either as gases or in a solvent. The malonamide was found to decompose with tertiary amines such as pyridine. Attempts to react the malonamide with carbonyl chloride, fluoride, and sulfide to form a barbiturate were unsuccessful. N-Phenyl-N’-pentafluorosulfanyl was prepared from pentafluorosulfanyl isocyanate and aniline. Attempts to prepare the mixed urea from pentafluorosulfanylamine and phenyl isocyanate failed. A possible product from a reaction of thiazyl trifluoride and aniline was either ΦN=S(F₂) ≡ N. Attempts to prepare N-pentafluorosulfanylurea from the reaction of SF₅NCO and NH₃ or SF₅NH₂ and HNCO failed.

Name thesis:degree_name

Master of Science

Level thesis:degree_level

masters

Discipline thesis:degree_discipline

Chemistry

Department dc:contributor.department

Chemistry

Grantor dc:publisher

Virginia Polytechnic Institute and State University

Year dc:date.issued

1974

Author dc:creator

• Shaddix, Robert Edwin

Statement dc:rights

• In Copyright

Licence dc:rights.uri

• http://rightsstatements.org/vocab/InC/1.0/

Language dc:language.iso

en

Handle dc:identifier.uri

http://hdl.handle.net/10919/70567

OAI identifier oai:identifier

oai:vtechworks.lib.vt.edu:10919/70567