The formation of α-amino- and α-hydroxy-alkanephosphonic acids in the reactions of phosphite esters with aldehydes and alkyl carbamates

Article abstract of DOI:10.1080/10426500008045250

The preparation of α-aminoalkanephosphonic acids from triphenyl phosphite, an aldehyde, and ethyl or benzyl carbamate in glacial acetic acid, followed by hydrolysis, is accompanied by the formation of the corresponding α-hydroxyphosphonic acid. Reaction in toluene, using boron trifluoride-etherate as catalyst, affords an alternative preparative procedure but does not prevent the formation of α-hydroxyphosphonic acid. ³¹P nmr reveals the presence of numerous intermediates. The reactions are discussed.

Full text of DOI:10.1080/10426500008045250

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Phosphorus, Sulfur, and Silicon
and the Related Elements
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THE FORMATION OF α-
AMINO AND α-HYDROXY-
ALKANEPHOSPHONIC ACIDS IN
THE REACTIONS OF PHOSPHITE
ESTERS WITH ALDEHYDES AND
ALKYL CARBAMATES
Harry R. Hudson a , Fatima Ismail a , Max Pianka a &
Chi-Wai Wan a
a Division of Chemistry, School of Biological and
Applied Sciences , University of North London ,
Holloway Road, London, N7 808, United Kingdom
Published online: 27 Oct 2006.
To cite this article: Harry R. Hudson , Fatima Ismail , Max Pianka & Chi-Wai Wan
(2000) THE FORMATION OF α-AMINO AND α-HYDROXY-ALKANEPHOSPHONIC ACIDS IN
THE REACTIONS OF PHOSPHITE ESTERS WITH ALDEHYDES AND ALKYL CARBAMATES,
Phosphorus, Sulfur, and Silicon and the Related Elements, 164:1, 245-257, DOI:
10.1080/10426500008045250
To link to this article: http://dx.doi.org/10.1080/10426500008045250
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