Chemospecific reaction of activated acetylenic compounds with triphenylphosphine in the presence of a system containing two functional groups

Abstract

A mild and efficient chemospecific method has been developed for the preparation of organophosphorus compounds, in good yields, through the reaction of 2-bromoacetamide or ethyl phenylcarbamate with PPh 3 in the presence of activated acetylenic esters.

A facile access to highly functionalized triphenylphosphoranylidene succinimides through a three-component reaction and DFT investigation of the reaction mechanism

“…Compound 6 should be exhibited two rotational isomers because of the ylide moiety in these compounds is strongly conjugated with the adjacent carbonyl group of an ester, and rotation about the partial double bond in the (E) and (Z) geometrical isomers is slow at room temperature (Scheme 3). [25][26][27] The mass spectra of product displayed initial fragmentation involved Ph-CO fragment which is not consistent with structures 6 and 7. The 1 H, 13 C and 31 P NMR spectra of the obtained products don't exhibit rotational isomers therefore, the correct structure of products can be characterized as compound 3 (Table 1).…”

Three-Component Reaction between Triphenylphosphine, Dialkyl Acetylenedicarboxylates and 3-(3,5-Dimethyl Pyrazol-1-yl)-3-oxo Propionitrile

“…1,2 Reaction of acetylenic esters with triphenylphosphine in the presence of an organic compound possessing an acidic-hydrogen has been recently reported to produce phosphorus ylides. [4][5][6] In continuation of our works on the reaction between triphenylphosphine and acetylene diesters in the presence of organic N-H, O-H or C-H acids, [7][8][9][10][11][12][13] we report here an efficient synthetic route to stable phosphorus ylides using three-component reactions between dialkyl acetylenedicarboxylates (DAAD's), triphenylphosphine and 3-(3,5-dimethyl pyrazol-1-yl)-3oxopropionitrile 3.…”

Three-Component Reaction between Triphenylphosphine, Dialkyl Acetylenedicarboxylates and N-Acetylarylidenehydrazides

“…1 Reaction of acetylenic esters with triphenylphosphine in the presence of an organic compound containing an acidichydrogen has also been reported to produce phosphorus ylides. [3][4][5][6] In continuation of our previous work on the reaction between phosphorus nucleophiles and acetylenic esters in the presence of organic acids, [7][8][9][10][11][12][13][14] we decided to investigate the reaction of N-acetylarylidenehydrazides with acetylenic esters in the presence of triphenylphosphine.…”