855525-63-2

Upstream product

• 116762-41-5 racemic N-t-butyl-P-phenylphosphonamidothioic acid 
• 186581-53-3 diazomethane 
• 116762-40-4 (S)-α-methylbenzylamine salt of N-t-butyl-P-phenylphosphonamidothioic acid 
• 74-88-4 methyl iodide 
• 116762-44-8 racemic N-t-butyl-P-phenylphosphonamidothioic chloride 
• 95980-86-2 t-butylamino-chlorophenylphosphane 
• 644-97-3 Dichlorophenylphosphine 

Downstream Products

• 15916-99-1 N,N'-Di-tert-butyl-P-phenylphosphonyldiamid 
• 84718-91-2 methyl N-t-butyl-P-phenylphosphonamidate 
• 116762-45-9 racemic N-t-butyl-N'-t-pentyl-P-phenylphosphonic diamide 
• 111783-64-3 racemic N-t-butyl-P-phenylphosphonamidic chloride 

Relevant academic research and scientific papers

Kinetic isotope effects of nitrogen and hydrogen in reaction of N-tert-butyl-P-phenylphosphonamidothioic acid with alcohols

Nitrogen and hydrogen isotope effects for the reaction of N-tert-butyl-P-phenylphosphonamidothioic acid 1 with alcohols (methanol, butanol, iso-propanol, tert-butanol) were measured in dichloromethane at 30 °C. The observed nitrogen isotope effect k14/k15 is only slightly sensitive to a steric hindrance of the alcohol [1.0070 ± 0.0002 (MeOH), 1.0074 ± 0.0004 (BuOH), 1.0062 ± 0.0004 (Pr iOH), 1.0087 ± 0.0007 (ButOH)]. The pre-equilibrium step, with proton transfer from oxygen to nitrogen was proved by the inverse hydrogen effect kROH/kROD[0.778 ± 0.052 (MeOH), 0.863 ± 0.063 (BuOH), 0.883 ± 0.080 (PriOH), 0.746 ± 0.084 (ButOH)]. The experimental values are consistent with theoretical results of semiempirical calculations on PM3 level for an elimination-addition mechanism and metathiophosphonate PhPSO intermediacy. For the reaction with methanol the addition-elimination mechanism is also possible.

Associative and Dissociative Mechanisms for the Rections of N-t-Butyl-P-phenylphosphonamidic Chloride with Isopropylamine and t-Butylamine: Competitive, Kinetic, and Stereochemical Studies

The substitution reactions of N-t-butyl-P-phenylphosphonamidic chloride (4a) with isopropylamine and t-butylamine (or t-pentylamine in stereochemical experiments) in MeCN at 0 deg C can apparently proceed by one associative and two dissociative mechanisms