ChemInform Abstract: RETRO-DIELS-ALDER REACTION IN MASS SPECTROMETRY

1984 ◽  
Vol 15 (37) ◽  
Author(s):  
F. TURECEK ◽  
V. HANUS
1977 ◽  
Vol 30 (5) ◽  
pp. 1061 ◽  
Author(s):  
R Bergamasco ◽  
QN Porter

3-Vinylindene, 2-methyl-3-vinylindene and 3-isopropenylindene give normal, photostable adducts with ethenetetracarbonitrile by a Diels- Alder process. The first diene gives adducts with maleic anhydride, N- phenylmaleimide and dimethyl acetylenedicarboxylate. Where there is stereochemical ambiguity the adducts are shown by mass spectrometry to be exclusively endo. Two heterocyclic analogues are formed from 3- vinylindene with p-toluenesulphonyl cyanide and N-sulphinyl-p- toluenesulphonamide.


1977 ◽  
Vol 30 (7) ◽  
pp. 1523 ◽  
Author(s):  
R Bergamasco ◽  
QN Porter

3-Vinylindene gives high yields of adducts with 1,4-benzoquinone, 1,4- naphthoquinone, and benzo[b]-thiophen 1,1-dioxide. The structures and stereochemistries of the adducts are confirmed by p.m.r. and mass spectrometry. The effects of various oxidation procedures on the 1,4- naphthoquinone adduct are described; no skeletal rearrangement accompanies oxidation with oxygen in base. Some adducts of 34sopropenylindene and 2-methyl-3-vinylindene are also described.


Author(s):  
Darya Hadavi ◽  
Peiliang Han ◽  
Maarten Honing

AbstractContinuous flow chemistry is an efficient, sustainable and green approach for chemical synthesis that surpasses some of the limitations of the traditional batch chemistry. Along with the multiple advantages of a flow reactor, it could be directly connected to the analytical techniques for on-line monitoring of a chemical reaction and ensure the quality by design. Here, we aim to use ion mobility, mass and tandem mass spectrometry (IMS-MS and MS/MS) for the on-line analysis of a pharmaceutically relevant chemical reaction. We carried out a model hetero-Diels Alder reaction in a microflow reactor directly connected to the IMS-MS and MS/MS using either electrospray or atmospheric pressure photo ionization methods. We were able to monitor the reaction mechanism of the Diels Alder reaction and structurally characterize the reaction product and synthesis side-products. The chosen approach enabled identification of two isomers of the main reaction product. A new strategy to annotate the ion mobility spectrum in the absence of standard molecules was introduced and tested for its validity. This was achieved by determining the survival yield of each isomer upon ion mobility separation and density functional theory calculations. This approach was verified by comparing the theoretically driven collision cross section values to the experimental data. In this paper, we demonstrated the potential of combined IMS-MS and MS/MS on-line analysis platform to investigate, monitor and characterize structural isomers in the millisecond time scale.


1984 ◽  
Vol 3 (1) ◽  
pp. 85-152 ◽  
Author(s):  
František Tureček ◽  
Vladimír Hanuš

2012 ◽  
Vol 554-556 ◽  
pp. 747-750
Author(s):  
Yu Jiang ◽  
Wen Guang Wang ◽  
Rui Cheng ◽  
Teng Zhou Yang ◽  
Jia Ling Pu

A novel dibromo-substituted HBC derivative, whose side chains contains oxygen heteroatoms, has been successfully synthesized by Diels-Alder reaction of asymmetric synthesis. It possesses bromo-functional groups to provide possibility to further synthesize more complex HBC derivatives. The final compound’s structure has been confirmed by1HNMR,13CNMR and MALDI-TOF mass spectrometry.


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