TY - JOUR
T1 - Unimolecular rearrangements of ketene-O,O-acetals and fragmentations occurring in the gas phase
AU - Morales-Ríos, Martha S.
AU - Lõpez-Camacho, Perla Y.
AU - Jacobo-Cabral, Carlos O.
AU - Pérez-Rojas, Nadia A.
AU - Trujillo-Serrato, Joel J.
AU - Burgueño-Tapia, Eleuterio
AU - Suárez-Castillo, Oscar R.
AU - Joseph-Nathan, Pedro
PY - 2011/5
Y1 - 2011/5
N2 - 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.
AB - 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.
KW - EI-ion trap
KW - gas phase rearrangement
KW - indole
KW - ketene acetal
KW - thermal decarbomethoxylation
UR - http://www.scopus.com/inward/record.url?scp=79954544084&partnerID=8YFLogxK
U2 - 10.1002/jms.1915
DO - 10.1002/jms.1915
M3 - Artículo
SN - 1076-5174
VL - 46
SP - 489
EP - 495
JO - Journal of Mass Spectrometry
JF - Journal of Mass Spectrometry
IS - 5
ER -