Alcoholysis of dialkyl tetrazolylphosphonites



: Nurminen EJ, Mattinen JK, Lonnberg H

Publisher: ROYAL SOC CHEMISTRY

: 1999

Royal Society of Chemistry. Journal: Perkin Transactions 2

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2

: J CHEM SOC PERK T 2

: 11

: 2551

: 2556

: 6

: 0300-9580

DOI: https://doi.org/10.1039/a904406j


Kinetics of the reaction of diisopropyl tetrazolylphosphonite with tert-butyl alcohol in dry THF have been studied in the presence of various acids, bases and salts that catalyze the process. Ammonium azolide salts were found to be considerably more efficient catalysts than the corresponding azole acids or tertiary amine bases. For instance, the relative rates obtained with N,N-diisopropylethylammonium tetrazolide, N,N-diisopropylethylamine and tetrazole were 104, 28 and 1, respectively. The salts of strong protolytes turned out to be better catalysts than those of weak ones. The susceptibility of the reaction rate to the pK(BH+) of the base is fairly strong (Bronsted beta = 0.41) compared to the sensitivity to the pK(a) of azoles (beta = 0.17). The mechanisms of catalysis are discussed.



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