Producción Científica Profesorado

Unimolecular rearrangements of ketene-O,O-acetals and fragmentations occurring in the gas phase



Suárez Castillo, Oscar Rodolfo

2011

Morales-Ríos Martha S., López-Camacho Perla Y., Jacobo-Cabral Carlos O., Pérez-Rojas Nadia A., Trujillo-Serrato Joel J., Burgueño-Tapia Eleuterio, Súarez-Castillo Oscar R., Joseph-Nathan Pedro. Unimolecular rearrangements of ketene-O,O-acetals and fragmentations occurring in the gas phase.J. Mass. Spectrom. 46, 489495 (2011). DOI 10.1002/jms.1915.


Abstract


Gas phase skeletal rearrangements of regioisomeric 3-cyano-2-methoxy-3a-alkylfuro[2,3-b]- and [3,2-b]indoles were evidenced by product ions [M ? 32]+, consistent with loss of methanol, on electron ionization in their mass spectra. The rearranged products occurring in gas phase were demonstrated to have elemental composition and fragmentation properties identical to those of authentic samples of 2-indolyl cyanomalonates. Isotopic labeling experiments support the formation mechanism of the [M ? 32]+ ion. Additional thermal gas-phase reaction products were characterized by comparison with an authentic sample.



Producto de Investigación




Artículos relacionados

Firsttotalsyntheses of dihydroflustramine C and flustramine E, alkaloids from the marine bryozoan Fl...

Reactivity of TpMe2Ir(C2H4)(DMAD) with carboxylic acids. A DFT study on geometrical isomers and stru...

Synthesis of 6-bromo-2-arylindoles using 2-iodobenzoic acid as precursor

Synthesis of Acetamido(indol-3-yl)propanol Derivatives

Cascade [1,3]-Sigmatropic Rearrangements of Ketene O,O-Acetals: Kinetic and DFT Level Mechanistic St...

Unimolecular rearrangements of ketene-O,O-acetals and fragmentations occurring in the gas phase

First Total Synthesis of ()-Flustraminol B

Synthesis of Bromoindole Alkaloids from Laurencia brongniartii

Preparation of 3-hydroxyoxindoles with dimethyldioxirane and their use for the synthesis of natural ...

Total Syntheses of Five Indole Alkaloids from the Marine Bryozoan Flustra foliacea