Part 2. Mechanistic aspects of the reduction of S-alkyl-thionocarbonates in the presence of triethylborane and air

Florent Allais, Jean Boivin and Van Tai Nguyen
Beilstein J. Org. Chem. 2007, 3, No. 46. https://doi.org/10.1186/1860-5397-3-46

Supporting Information

Supporting Information File 1: Procedure for the preparation of deuterated triethylboranes, Procedures for the reduction with deuterated triethylboranes. Preparation of deuterated Et3B (d-15, d-9, and d-6).
Format: PDF Size: 79.0 KB Download
Supporting Information File 2: Part 2. Mechanistic aspects of the reduction of S-alkyl-thionocarbonates in the presence of triethylborane and air. Detailed procedures for preparation of new compounds and their spectroscopic data, pp 1–10.
Format: PDF Size: 607.5 KB Download
Supporting Information File 3: Part 2. Mechanistic aspects of the reduction of S-alkyl-thionocarbonates in the presence of triethylborane and air. Detailed procedures for preparation of new compounds and their spectroscopic data, pp 11–43.
Format: PDF Size: 9.5 MB Download
Supporting Information File 4: Part 2. Mechanistic aspects of the reduction of S-alkyl-thionocarbonates in the presence of triethylborane and air. Detailed procedures for preparation of new compounds and their spectroscopic data, pp 44–56.
Format: PDF Size: 2.1 MB Download

Cite the Following Article

Part 2. Mechanistic aspects of the reduction of S-alkyl-thionocarbonates in the presence of triethylborane and air
Florent Allais, Jean Boivin and Van Tai Nguyen
Beilstein J. Org. Chem. 2007, 3, No. 46. https://doi.org/10.1186/1860-5397-3-46

How to Cite

Allais, F.; Boivin, J.; Nguyen, V. T. Beilstein J. Org. Chem. 2007, 3, No. 46. doi:10.1186/1860-5397-3-46

Download Citation

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.

Citations to This Article

Up to 20 of the most recent references are displayed here.

Scholarly Works

  • Chatgilialoglu, C.; Barata-Vallejo, S.; Gimisis, T. Radical Reactions in Organic Synthesis: Exploring in-, on-, and with-Water Methods. Molecules (Basel, Switzerland) 2024, 29, 569. doi:10.3390/molecules29030569
  • Frolov, S. M.; Basevich, V. Y.; Belyaev, A. A.; Shamshin, I. O.; Aksenov, V. S.; Frolov, F. S.; Storozhenko, P. A.; Guseinov, S. L. Kinetic Model and Experiment for Self-Ignition of Triethylaluminum and Triethylborane Droplets in Air. Micromachines 2022, 13, 2033. doi:10.3390/mi13112033
  • Shevchenko, V. P.; Nagaev, I. Y.; Myasoedov, N. F. Incorporation of Hydrogen Isotopes into Biologically Active Compounds. Radiochemistry 2022, 64, 433–481. doi:10.1134/s1066362222040014
  • Marino, C.; Bordoni, A. V. Deoxy sugars. General methods for carbohydrate deoxygenation and glycosidation. Organic & biomolecular chemistry 2022, 20, 934–962. doi:10.1039/d1ob02001c
  • André‐Joyaux, E.; Gnägi, L.; Gnägi‐Lux, M.; Becerra, C. A. M.; Soulard, V.; Tappin, N. D. C.; Renaud, P. doi:10.1002/9780470682531.pat0978
  • Hayashi, H.; Kaga, A.; Wang, B.; Gagosz, F.; Chiba, S. Use of a benzyl ether as a traceless hydrogen donor in the anti-Markovnikov hydrofunctionalization of alkenes with xanthates. Chemical communications (Cambridge, England) 2018, 54, 7535–7538. doi:10.1039/c8cc02971g
  • Soulard, V.; Villa, G.; Vollmar, D. P.; Renaud, P. Radical Deuteration with D 2 O: Catalysis and Mechanistic Insights. Journal of the American Chemical Society 2017, 140, 155–158. doi:10.1021/jacs.7b12105
  • Anthore-Dalion, L.; Zard, S. Z. Chemoselective Reduction: Xanthates as Traceless Precursors of Polyfunctionalized α,α-Dichloroketones. Organic letters 2017, 19, 5545–5548. doi:10.1021/acs.orglett.7b02636
  • Jenkins, E. N.; Czaplyski, W. L.; Alexanian, E. J. A General Approach to Quaternary Center Construction from Couplings of Unactivated Alkenes and Acyl Xanthates. Organic letters 2017, 19, 2350–2353. doi:10.1021/acs.orglett.7b00882
  • Czaplyski, W. L.; Na, C. G.; Alexanian, E. J. C-H Xanthylation: A Synthetic Platform for Alkane Functionalization. Journal of the American Chemical Society 2016, 138, 13854–13857. doi:10.1021/jacs.6b09414
  • Povie, G.; Ford, L.; Pozzi, D.; Soulard, V.; Villa, G.; Renaud, P. Catechols as Sources of Hydrogen Atoms in Radical Deiodination and Related Reactions. Angewandte Chemie 2016, 128, 11387–11391. doi:10.1002/ange.201604950
  • Povie, G.; Ford, L.; Pozzi, D.; Soulard, V.; Villa, G.; Renaud, P. Catechols as Sources of Hydrogen Atoms in Radical Deiodination and Related Reactions. Angewandte Chemie (International ed. in English) 2016, 55, 11221–11225. doi:10.1002/anie.201604950
  • Curran, D. P.; McFadden, T. R. Understanding Initiation with Triethylboron and Oxygen: The Differences between Low-Oxygen and High-Oxygen Regimes. Journal of the American Chemical Society 2016, 138, 7741–7752. doi:10.1021/jacs.6b04014
  • Chenneberg, L.; Baralle, A.; Daniel, M.; Fensterbank, L.; Goddard, J.-P.; Ollivier, C. Visible Light Photocatalytic Reduction of O-Thiocarbamates: Development of a Tin-Free Barton–McCombie Deoxygenation Reaction. Advanced Synthesis & Catalysis 2014, 356, 2756–2762. doi:10.1002/adsc.201400729
  • Bruyère, I.; Tóth, Z.; Benyahia, H.; Xue, J. L.; Praly, J.-P. NaBH3CN and other systems as substitutes of tin and silicon hydrides in the light or heat-initiated reduction of halosugars: a tunable access to either 2-deoxy sugars or 1,5-anhydro-itols. Tetrahedron 2013, 69, 9656–9662. doi:10.1016/j.tet.2013.09.032
  • Povie, G.; Marzorati, M.; Bigler, P.; Renaud, P. Role of equilibrium associations on the hydrogen atom transfer from the triethylborane-methanol complex. The Journal of organic chemistry 2013, 78, 1553–1558. doi:10.1021/jo302576c
  • McCombie, S. W.; Motherwell, W. B.; Tozer, M. J. Organic Reactions - The Barton-McCombie Reaction. Organic Reactions 2012, 161–432. doi:10.1002/0471264180.or077.02
  • Lam, K.; Markó, I. E. Toluates: unexpectedly versatile reagents. Tetrahedron 2009, 65, 10930–10940. doi:10.1016/j.tet.2009.09.111
  • Povie, G.; Villa, G.; Ford, L.; Pozzi, D.; Schiesser, C. H.; Renaud, P. Role of catechol in the radical reduction of B-alkylcatecholboranes in presence of methanol. Chemical communications (Cambridge, England) 2009, 46, 803–805. doi:10.1039/b917004a
  • Rowlands, G. J. Radicals in organic synthesis. Part 1. Tetrahedron 2009, 65, 8603–8655. doi:10.1016/j.tet.2009.07.001
Other Beilstein-Institut Open Science Activities