47468-15-5Relevant academic research and scientific papers
Synthesis, properties and application of electronically-tuned tetraarylarsonium salts as phase transfer catalysts (PTC) for the synthesis of gem-difluorocyclopropanes
Grudzień, Krzysztof,Basak, Tymoteusz,Barbasiewicz, Micha?,Wojciechowski, Tomasz M.,Fedoryński, Micha?
supporting information, p. 106 - 110 (2017/04/11)
Preparation of gem-difluorocyclopropane from α-methylstyrene and chlorodifluoromethane was investigated under basic two-phase conditions. Although simple tetraalkylammonium salts appeared uneffective as phase-transfer catalysts (PTC) for this purpose, tetraphenylarsonium chloride displayed moderate activity, and inspired studies of the phenomena. To improve its efficiency we synthesized set of electronically-tuned tetraarylarsonium analogues. Their preparation revealed interesting exchange process of aryl substituents on the arsonium center, whereas activity studies demonstrated a correlation of catalytic efficiency with electronic effects of the substituents. Two of the tetraarylarsonium catalysts were characterized by X-ray studies.
TRITOLYLARSONIUM AND TRIS(METHOXYPHENYL)ARSONIUM YLIDES THE EFFECTS OF ortho-SUBSTITUENTS IN TRIARYLARSONIUM GROUPS ON THE PROPERTIES OF YLIDES
Harris, Gordon S.,Lloyd, Douglas,MacDonald, William A.,Gosney, Ian
, p. 297 - 304 (2007/10/02)
A number of tritolylarsonium and tris(methoxyphenyl)arsonium cyclopentadienylides and other ylides have been prepared and their properties (basicity, NMR spectra, reactions with aldehydes and nitrosobenzene, acetylation, and methanolysis) have been investigated.Substituents in the m- or p-positions of triarylarsonium groups have little effect on properties, but o-substituents result in markedly lower reactivity and lower basicity, and these ylides were also more difficult to prepare.NMR spectra gave indication of crowding in some of these o-substituted ylides.The effects of the o-substituents are discussed. p-Methyl- and p-methoxy-substituents increased the proportion of anil to ketoxime formed in reactions with nitrosobenzene, but the o-methoxy analogue gave only ketoxime.
