Electronic effect of substituents and mechanism on the formation of diethyl 3-oxo-3-arylpropyl phosphonates

Article abstract of DOI:10.1080/10426509708043563

The reaction of aryl β-chloroethyl ketones with triethyl phosphite to give γ-ketophosphonates was studied kinetically. This reaction follows a second order overall and involves a carbonyl group-assisted (CGA) initializing step, followed by a stereoselective pathway to γ-ketophosphonates. A linear Hammett plot reveals that the p value is 1.51 (r=0.994), and the transition state is accelerated by the para-halogen on the phenyl group. The results confirm the two-stage mechanism and rule out an S_N2 mechanism being responsible for the formation of diethyl 3-oxo-3-arylpropyl phosphonates 3.

Full text of DOI:10.1080/10426509708043563

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Phosphorus, Sulfur, and Silicon and the
Related Elements
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ELECTRONIC EFFECT OF SUBSTITUENTS
AND MECHANISM ON THE FORMATION
OF DIETHYL 3-OXO-3-ARYLPROPYL
PHOSPHONATES
Jen-Wen Yu a , Chien-Keun Chong a & Steve K. Huang a
a Graduate School of Chemical Engineering, National Taiwan University
of Science and Technology , Taipei, Taiwan, 106, Republic of CHINA
Published online: 04 Oct 2006.
To cite this article: Jen-Wen Yu , Chien-Keun Chong & Steve K. Huang (1997) ELECTRONIC
EFFECT OF SUBSTITUENTS AND MECHANISM ON THE FORMATION OF DIETHYL 3-OXO-3-ARYLPROPYL
PHOSPHONATES, Phosphorus, Sulfur, and Silicon and the Related Elements, 126:1, 235-242, DOI:
10.1080/10426509708043563
To link to this article: http://dx.doi.org/10.1080/10426509708043563
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