Display options
Cite
Stockinger S, Trapp O. Integrating reaction and analysis: investigation of higher-order reactions by cryogenic trapping. Beilstein J Org Chem. 2013;9:1837-42doi: 10.3762/bjoc.9.214.
Stockinger, S., & Trapp, O. (2013). Integrating reaction and analysis: investigation of higher-order reactions by cryogenic trapping. Beilstein journal of organic chemistry, 91837-42. https://doi.org/10.3762/bjoc.9.214
Stockinger, Skrollan, and Trapp, Oliver. "Integrating reaction and analysis: investigation of higher-order reactions by cryogenic trapping." Beilstein journal of organic chemistry vol. 9 (2013): 1837-42. doi: https://doi.org/10.3762/bjoc.9.214
Stockinger S, Trapp O. Integrating reaction and analysis: investigation of higher-order reactions by cryogenic trapping. Beilstein J Org Chem. 2013 Sep 10;9:1837-42. doi: 10.3762/bjoc.9.214. eCollection 2013. PMID: 24062850; PMCID: PMC3778332.
Copy Download .nbib Format: NLM
Share it on

Beilstein J Org Chem. 2013 Sep 10;9:1837-42. doi: 10.3762/bjoc.9.214. eCollection 2013.

Integrating reaction and analysis: investigation of higher-order reactions by cryogenic trapping.

Beilstein journal of organic chemistry

Skrollan Stockinger, Oliver Trapp

Affiliations

  1. Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany.

PMID: 24062850 PMCID: PMC3778332 DOI: 10.3762/bjoc.9.214

Abstract

A new approach for the investigation of a higher-order reaction by on-column reaction gas chromatography is presented. The reaction and the analytical separation are combined in a single experiment to investigate the Diels-Alder reaction of benzenediazonium-2-carboxylate as a benzyne precursor with various anthracene derivatives, i.e. anthracene, 9-bromoanthracene, 9-anthracenecarboxaldehyde and 9-anthracenemethanol. To overcome limitations of short reaction contact times at elevated temperatures a novel experimental setup was developed involving a cooling trap to achieve focusing and mixing of the reactants at a defined spot in a fused-silica capillary. This trap functions as a reactor within the separation column in the oven of a gas chromatograph. The reactants are sequentially injected to avoid undefined mixing in the injection port. An experimental protocol was developed with optimized injection intervals and cooling times to achieve sufficient conversions at short reaction times. Reaction products were rapidly identified by mass spectrometric detection. This new approach represents a practical procedure to investigate higher-order reactions at an analytical level and it simultaneously provides valuable information for the optimization of the reaction conditions.

Keywords: Diels–Alder reaction; benzyne; cryogenic CO2 trap; cycloaddition; flow chemistry; gas chromatography; on-column reaction gas chromatography

References

  1. Anal Chem. 2011 Sep 1;83(17):6485-92 - PubMed
  2. Anal Bioanal Chem. 2006 Jun;385(3):416-8 - PubMed
  3. Electrophoresis. 2012 Mar;33(6):1060-7 - PubMed
  4. Electrophoresis. 2010 Mar;31(5):786-813 - PubMed
  5. Anal Chem. 2013 Jan 15;85(2):557-78 - PubMed
  6. Chemistry. 2008;14(15):4657-66 - PubMed
  7. J Am Chem Soc. 2011 Oct 19;133(41):16444-50 - PubMed
  8. Chemistry. 2006 May 24;12(16):4407-16 - PubMed
  9. Nature. 2006 Jun 8;441(7094):705 - PubMed
  10. Chemistry. 2006 Aug 7;12(23):5972-90 - PubMed
  11. J Org Chem. 2009 Jun 5;74(11):4137-42 - PubMed
  12. Anal Bioanal Chem. 2009 Nov;395(6):1673-9 - PubMed
  13. Chem Commun (Camb). 2011 Jan 7;47(1):391-3 - PubMed
  14. J Chromatogr A. 2008 Mar 14;1184(1-2):160-90 - PubMed
  15. Chemistry. 2003 Dec 5;9(23):5708-23 - PubMed
  16. J Org Chem. 2006 Nov 24;71(24):9241-3 - PubMed

Publication Types