61958-39-2Relevant academic research and scientific papers
Hetaryl-substituted phosphonium-iodonium ylides in synthesis of heterocycles
Matveeva, Elena D.,Podrugina, Tatyana A.,Taranova, Marina A,Ivanova, Anastasiya M.,Gleiter, Rolf,Zefirov, Nikolay S.
experimental part, p. 5770 - 5774 (2012/09/07)
A series of hitherto unknown hetaryl-substituted (in phosphonium part) phosphonium-iodonium ylides were synthesized. The reaction of these mixed phosphonium-iodonium ylides with acetylenes opens a way to new furyl annelated phosphinolines or unusually substituted phosphininofurans.
Photochemical synthesis of phosphinolines from phosphonium-iodonium ylides
Matveeva, Elena D.,Podrugina, Tatyana A.,Taranova, Marina A.,Borisenko, Anatolyi A.,Mironov, Andrey V.,Gleiter, Rolf,Zefirov, Nikolay S.
experimental part, p. 566 - 572 (2011/04/16)
We describe three different series of experiments which were undertaken to test our hypothesis that during irradiation of phosphonium-iodonium ylides (1a, 1b) an electrophilic carbene is generated. By opposing the assumed intermediate to monosubstituted alkynes, we observed in the case of electron-rich substituents at the triple bond a domination of a 1,3-dipolar cycloaddition of the intermediate with the triple bond to yield furans. In the case of electron poorer substituents, the formation of phosphinolines prevails. A second series of experiments was carried out with mixed ylides in which one phenyl ring at the triarylphosphonium group was replaced by a thienyl group. In this case, we observe only an intramolecular reaction with the thienyl ring to yield the phosphinolines 21-23. In a third test, we replaced in the mixed ylides 1a, 1b the COR group by a CN substituent. This modification leads to phosphinolines only and avoids a 1,3-dipolar cycloaddition.
