Phosphorus, Sulfur and Silicon and the Related Elements p. 1017 - 1027 (2009)
Update date:2022-08-02
Topics:
Mazurkiewicz, Roman
Pazdzierniok-Holewa, Agnieszka
Grymel, Mirosawa
4-Phosphoranylidene-5(4H)-oxazolones 1 undergo hydrolysis in THF in the presence of HBF4 at room temperature to give N-acyl-α- triphenyphosphonioglycines 3 (R2 = H) in very good yields. 4-Alkyl-4- triphenylphosphonio-5(4H)-oxazolones 2 react with water in CH2Cl 2/THF solution without any acidic catalyst at 0-5°C in a few days yielding N-acyl-α-triphenylphosphonio-α-amino acids 3 (R 2 = Me) or α-(N-acylamino)alkyltriphenylphosphonium salts 4 (R2 = alkyl, other then Me).-Triphenylphosphonio-α-amino acids 3 upon heating to 105-115°C under reduced pressure (5 mm Hg) or upon treatment with a Hunig base in CH2Cl2 at 20°C undergo decarboxylation to give the corresponding α-(N-acylamino)-alkyltriphenylphosphonium salts 4, usually in very good yields.
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