Abstract
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-phenylenedioxyasenate(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.
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