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...

The one-carbon ring expansion of 1-deoxy-1-thio-1,6-anhydrosugars, mediated by metal carbenes and proceeding through the intermediacy of sulfur ylides, has been proposed as a route for the synthesis of the tagetitoxin skeleton. Intermolecular reactions of such thioanhydrosugars with diazoesters afford a range of undesired products derived from the initially formed ylide, whereas use of an intra...

We report the use of a cyclic carbodiphosphorane catalyst for ketone and imine hydroboration reactions. Ketone reactions are particularly rapid, typically reaching completion within 15 min using 1 mol % loading at 25 °C. To our knowledge, this represents first as an organocatalyst. The exhibited superior catalytic activity in comparison to other neutral carbon nucleophiles tested, including N-h...

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...

This so-called Wittig reaction has a number of advantages over other olefination methods; in particular, it occurs with total positional selectivity (that is, an alkene always directly replaces a carbonyl group). By comparison, a number of other carbonyl olefination reactions often occur with double-bond rearrangement. In addition, the factors that influence Eand Z-stereoselectivity are well un...

The synthesis and reactivity of tetrazol-5-yl-phosphorus ylides towards N-halosuccinimide/TMSN₃ reagent systems was explored, opening the way to new haloazidoalkenes bearing a tetrazol-5-yl substituent. These compounds were obtained as single isomers, except in one case. X-ray crystal structures were determined for three derivatives, establishing that the non-classical Wittig reaction leads to ...

Results of research into four-membered 2-halo-1,2λ⁵-oxaphosphetane phosphorus(V)-heterocycles are presented. The preparation of 2-halo-1,2λ⁵-oxaphosphetanes by reaction of P-haloylides with carbonyl compounds is described. The mechanism of asynchronous [2+2]-сycloaddition of ylides to aldehydes was proposed on the base of low-temperature NMR investigations. 2-Halo-1,2λ⁵-oxaphosphetanes were iso...