DOI: 10.1002/anie.200460059. Probing the Mechanism of the Baylis–Hillman Reaction by Electrospray Ionization Mass and Tandem Mass Spectrometry

Probing the Mechanism of the Baylis–Hillman Reaction by Electrospray Ionization Mass and Tandem Mass Spectrometry

10.1002/anie.200460059

Crossref journal-article

Wiley

Angewandte Chemie International Edition (311)

Bibliography

Santos, L. S., Pavam, C. H., Almeida, W. P., Coelho, F., & Eberlin, M. N. (2004). Probing the Mechanism of the BaylisâHillman Reaction by Electrospray Ionization Mass and Tandem Mass Spectrometry. Angewandte Chemie International Edition, 43(33), 4330â4333. Portico.

Authors 5

Leonardo Silva Santos (first)
Cesar Henrique Pavam (additional)
Wanda P. Almeida (additional)
Fernando Coelho (additional)
Marcos N. Eberlin (additional)

References 77 Referenced 263

10.1002/(SICI)1521-3757(20000103)112:1<46::AID-ANGE46>3.0.CO;2-P
10.1002/(SICI)1521-3773(20000103)39:1<44::AID-ANIE44>3.0.CO;2-L
10.1002/ange.19911030504
10.1002/anie.199104553
10.1002/ange.19951070304
10.1002/anie.199502591
For comprehensive reviews on the Baylis–Hillman reaction see:
10.1021/cr010043d
10.1590/S0100-40422000000500006 / Quim. Nova by Almeida W. P. (2000)
{'key': 'e_1_2_2_7_3', 'first-page': '236562e', 'volume': '132', 'year': '2000', 'journal-title': 'Chem. Abstr.'} / Chem. Abstr. (2000)
{'key': 'e_1_2_2_8_2', 'first-page': '201', 'volume': '51', 'author': 'Ciganek E.', 'year': '1997', 'journal-title': 'Org. React.'} / Org. React. by Ciganek E. (1997)
10.1016/0040-4020(96)00154-8
10.1246/bcsj.41.2815
A. B.Baylis M. E. D.Hillman German Patent 2155113 1972[
{'key': 'e_1_2_2_11_3', 'first-page': '34174q', 'volume': '77', 'year': '1972', 'journal-title': 'Chem. Abstr.'} / Chem. Abstr. (1972)
For some examples see:
10.1016/S0040-4039(02)02765-X
10.1081/SCC-120017189
10.1016/S0040-4039(02)00351-9
10.1016/S0040-4020(01)00647-0
10.1039/b106471c
10.1016/S0040-4039(01)01676-8
10.1081/SCC-100104463
{'key': 'e_1_2_2_20_2', 'first-page': '57', 'volume': '39', 'author': 'Ameer F.', 'year': '1986', 'journal-title': 'S. Afr. J. Chem.'} / S. Afr. J. Chem. by Ameer F. (1986)
10.1002/hlca.19840670209
10.1021/jo00220a034
10.1039/p19820002079
10.1002/poc.610030503
10.1002/ange.19830951007
10.1002/anie.198307961
10.1016/0040-4039(91)80098-Q
10.1016/S0040-4020(01)88227-2
10.1080/00397919308012600
10.1021/ac00280a023
10.1126/science.2675315
{'key': 'e_1_2_2_32_2', 'volume-title': 'Electrospray Ionization Mass Spectroscopy', 'author': 'Cole R. B.', 'year': '1997'} / Electrospray Ionization Mass Spectroscopy by Cole R. B. (1997)
10.1021/ac010284l
10.1002/ange.200351210
10.1002/anie.200351210
M. N. Eberlin F. C. Gozzo C. S. Consorti J. Dupont Chem. Eur. J.2004 in press. (10.1055/s-2004-822372)
10.1002/1521-3757(20020517)114:10<1797::AID-ANGE1797>3.0.CO;2-V
10.1002/1521-3773(20020517)41:10<1721::AID-ANIE1721>3.0.CO;2-5
10.1021/ac0344384
10.1021/ac010284l
10.1002/1521-3757(20020802)114:15<2863::AID-ANGE2863>3.0.CO;2-I
10.1002/1521-3773(20020802)41:15<2738::AID-ANIE2738>3.0.CO;2-X
10.1002/ange.200353076
10.1002/anie.200353076
10.1007/s00216-003-2230-5
M. N. Eberlin J. B. Domingos E. Longhinotti T. A. S. Brandão C. A. Bunton L. S. Santos F. Nome J. Org. Chem.2004 in press.
10.1002/(SICI)1521-3757(19981002)110:19<2831::AID-ANGE2831>3.0.CO;2-E
10.1002/(SICI)1521-3773(19981016)37:19<2685::AID-ANIE2685>3.0.CO;2-M
10.1002/ange.200200560
10.1002/anie.200200560
The mass spectrometer was a high‐resolution hybrid double quadrupole (Qq) and orthogonal time‐of‐flight (TOF) mass spectrometer (QTOF Micromass UK). The temperature of the nebulizer was 50 °C. The ESI source and the mass spectrometer were operated in the positive‐ion mode. The cone and extractor potentials were set to 40–45 and 5–10 V respectively. The scan range wasm/z50–1000.
10.1016/S0040-4039(98)01927-3
10.1016/S0040-4020(02)00822-0
10.1016/S0040-4039(03)01307-8
10.3998/ark.5550190.0004.a42
10.1016/j.ica.2004.01.011
B. A. da Silveira Neto G. Ebeling R. S. Gonçalves F. C. Gozzo M. N. Ebelin J. Dupont Syntheses2004 1155–1158; (10.1055/s-2004-822372)
10.1016/j.ica.2003.12.025
Cleavage of electrostatic ion/neutral interactions such as those operating in proton‐bonded dimers has been shown to be invariably much more efficient than the breaking of stronger covalent bonds of gas‐phase ions see for example:
10.1021/ar960242x
10.1021/ja00085a028
10.1021/jo980421n
10.1016/S0040-4020(01)00316-7
10.1039/b203079a
10.1002/(SICI)1098-2787(1997)16:3<113::AID-MAS1>3.0.CO;2-K

Dates

Type	When
Created	21 years ago (Aug. 13, 2004, 12:40 p.m.)
Deposited	1 year, 10 months ago (Oct. 11, 2023, 1:17 p.m.)
Indexed	6 days, 8 hours ago (Aug. 29, 2025, 6:40 a.m.)
Issued	21 years ago (Aug. 13, 2004)
Published	21 years ago (Aug. 13, 2004)
Published Online	21 years ago (Aug. 13, 2004)
Published Print	21 years ago (Aug. 20, 2004)

Funders 0

None

BibTeX

@article{Santos_2004, title={Probing the Mechanism of the Baylis–Hillman Reaction by Electrospray Ionization Mass and Tandem Mass Spectrometry}, volume={43}, ISSN={1521-3773}, url={http://dx.doi.org/10.1002/anie.200460059}, DOI={10.1002/anie.200460059}, number={33}, journal={Angewandte Chemie International Edition}, publisher={Wiley}, author={Santos, Leonardo Silva and Pavam, Cesar Henrique and Almeida, Wanda P. and Coelho, Fernando and Eberlin, Marcos N.}, year={2004}, month=aug, pages={4330–4333} }

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