On the behaviour of sulfonates towards As(III) nucleophiles

Article abstract of DOI:10.1080/10426509808033725

Mesylates and hydrophilic amsylates and [3]betylates were tried as substrates in an effort to create a C-As bond. In no case did we detect the formation of arsonic acids. With Na₃AsO₃ as nucleophile the product was the parent alcohol due to exclusive attack of the HO^- present in the aqueous Na₃AsO₃. With (PhS)₃As as the nucleophile in the absence of Lewis acid catalyst the products were diphenyl disulfide and AS₂O₃ while in the presence of catalyst alkyl phenyl sulfide was obtained, implying that the electron pair on As was chemically inactive. As₂O₃ did not react with these electrophiles, and potassium di-O-phenylenedioxyarsenate(III) was unreactive towards alkyl bromides but it gave the monoalkyl ether of catechol with amsylates and [3]betylates, again implying that the stereochemically active electron pair of As was not chemically active.

Full text of DOI:10.1080/10426509808033725

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Phosphorus, Sulfur, and Silicon
and the Related Elements
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ON THE BEHAVIOUR OF
SULFONATES TOWARDS AS(III)
NUCLEOPHILES
a
Gerasimos M. Tsivgoulis , Demetrios N. Sotiropoulos
a
a
&
Panayiotis V. Ioannou
a
Department of Chemistry , University of Patras ,
Patras, Greece
Published online: 24 Sep 2006.
To cite this article: Gerasimos M. Tsivgoulis , Demetrios N. Sotiropoulos & Panayiotis
V. Ioannou (1998) ON THE BEHAVIOUR OF SULFONATES TOWARDS AS(III) NUCLEOPHILES,
Phosphorus, Sulfur, and Silicon and the Related Elements, 141:1, 97-110, DOI:
10.1080/10426509808033725
To link to this article: http://dx.doi.org/10.1080/10426509808033725
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