TY - JOUR
T1 - Fragmentation of methyl hydrogen α-hydroxyiminophosphonates to monomeric methyl metaphosphate
T2 - Stereochemistry and mechanism
AU - Katzhendler, Jehoshua
AU - Karaman, Rafik
AU - Gibson, Dan
AU - Breuer, Eli
AU - Leader, Haim
PY - 1989
Y1 - 1989
N2 - Methyl α-(hydroxyimino)benzylphosphonates [(E)-(2) and (Z)-(2)] undergo fragmentation in alcohols to benzonitrile and a (mixed) phosphodiester. Kinetic studies of the behaviour of (E)-(2) and (Z)-(2) in a series of alcohols indicate that (Z)-(2) undergoes acid catalysed isomerization to (E)-(2) which subsequently undergoes fragmentation via a concerted, dissociative bond cleavage to benzonitrile and monomeric methyl metaphosphate (7). The latter is trapped by the solvent in the second step of the reaction to give the final phosphodiester product.
AB - Methyl α-(hydroxyimino)benzylphosphonates [(E)-(2) and (Z)-(2)] undergo fragmentation in alcohols to benzonitrile and a (mixed) phosphodiester. Kinetic studies of the behaviour of (E)-(2) and (Z)-(2) in a series of alcohols indicate that (Z)-(2) undergoes acid catalysed isomerization to (E)-(2) which subsequently undergoes fragmentation via a concerted, dissociative bond cleavage to benzonitrile and monomeric methyl metaphosphate (7). The latter is trapped by the solvent in the second step of the reaction to give the final phosphodiester product.
UR - http://www.scopus.com/inward/record.url?scp=37049074347&partnerID=8YFLogxK
U2 - 10.1039/p29890000589
DO - 10.1039/p29890000589
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AN - SCOPUS:37049074347
SN - 1472-779X
SP - 589
EP - 594
JO - Journal of the Chemical Society, Perkin Transactions 2
JF - Journal of the Chemical Society, Perkin Transactions 2
IS - 6
ER -