A general preparation of new types of benzofurans, benzothiophenes and indoles is realized via chemoselective intramolecular Wittig reactions with the corresponding ester, thioester and amide functionalities using in situ formed phosphorus ylides as key intermediates. The reaction conditions are very mild, and numerous Michael acceptors and commercially available acid chlorides can be applied v...

The reaction of ferrocenyldiphenylphosphine with styrene oxide in ethanol gives, as the major product, ferrocenyl(phenyl)(l,2-diphenylethyl)phosphine oxide (5, R = Ph), the result of a rearrangement involving phenyl migration from phosphorus to adjacent carbon in the decomposition of a vinylphosphonium ion arising from protonation and subsequent elimination of water from the initially-formed ph...

protonation of the highly reactive 1:1 intermediates, produced in the reaction between triphenylphosphine and acetylenic esters, by nh-acids such as azathioprine, imidazole or theophylline leads to the formation of vinyltriphenylphosphonium salts, which undergo a michael addition reaction with a conjugate base to produce phosphorus ylides. silica nanoparticles (silica nps were prepared by therm...

An efficient synthesis of tetrasubstituted furans was achieved from the corresponding α,β-unsaturated ketone derivatives, acid chlorides, and Bu3P in the presence of Et3N via a chemoselective intramolecular Wittig reaction as the key step. The presence of an additional electron-withdrawing group in the α-position of Michael acceptors controlled the chemoselectivities of presumable phosphorus yl...

Alkene cis-trans Ratio, Betaine Mechanism, Cycloaddition Mechanism The cis-trans ratio of the stilbenes formed in Wittig reactions of semistabilised ylides (derived from benzyltri(hetero)arylphosphonium salts in ethanolic ethoxide) with benzaldehyde decreases markedly in the series 2-furyl >2-thienyl >phenyl > 1-methylpyrrol2-yl. The 2-furyl group favours a greater proportion of the ci«-isomer ...

A new and general strategy for highly functional furo[3,4-c]coumarins and related furyl coumarin derivatives has been developed, which is based on an extraordinarily facile intramolecular Wittig reaction, starting from α,β-unsaturated ketones, tributylphosphine, and acyl chlorides. The phosphorus ylides were proposed to be the key intermediates for constructing the crucial furan ring, leading t...

The main synthetic routes towards vinylphosphonium salts and their wide applications in organic synthesis are discussed in this review. Particular attention is paid to the use of these compounds as building blocks for the synthesis of carbo- and heterocyclic systems after their prior transformation into the corresponding phosphorus ylides, followed by the intramolecular Wittig reaction with var...

Many useful organic reactions have been developed by taking advantage of the high affinity phosphorus atoms with some heteroatoms such as oxygen and sulfur atoms. Although proceed via ylides, phosphonium salts phosphoranyl radicals active species, are only a few reports. In this short review, three reported recently described.

kinetic studies were made of the reactions between triphenylphosphine 1, dialkyl acetylenedicarboxylates 2 in the presence of nh-acid, such as maleimid (as a protic/nucleophilic reagent) 3. to determine the kinetic parameters of the reactions, they were monitored by uv spectrophotometery. the second order fits were automatically drawn and the values of the second order rate constant (k2) were a...