340
Views
2
CrossRef citations to date
0
Altmetric
Short Communication

Selective and efficient desulfurization of thiiranes with Mo(CO)6

&
Pages 13-18 | Received 06 Jun 2019, Accepted 06 Aug 2019, Published online: 16 Aug 2019

References

  • Chung-Yang H, Abigail G. The chemistry of transition metals with three-membered ring heterocycles. Chem Rev. 2014;114:8153–8198. doi: 10.1021/cr500036t
  • Wilfried-Solo O, Francois YP, Schollhammer P, et al. Carbon-sulfur and carbon-halogen bond cleavage of acyclic or cyclic thioethers, thiophenes, and dihaloalkanes with the trithiolato-bridged cation [Mo2Cp2(μ-SMe)3(MeCN)2]. Organometallics. 2010;29:448–462. doi: 10.1021/om900901s
  • Nalet’ko SA, Pervova MG, Gorbunova TI, et al. Thermal desulfurization of (alkoxymethyl) thiiranes. Russ J Gen Chem. 2014;84:2120–2124. doi: 10.1134/S1070363214110139
  • Takako M, Tomoko N, Atsushi N, et al. Reactions of (Silyl)(silylene)tungsten and molybdenum complexes with sulfur reagents. Organometallics. 2010;29:6624–6626. doi: 10.1021/om100875h
  • Proulx G, Robert GB. Synthesis of alkyltantalocene oxide, sulfide, and imide derivatives: stereospecific heteroatom and –group transfers from oxiranes, thiiranes, and aziridines to methyltantalocene. Organometallics. 1996;15:133–141. doi: 10.1021/om950470f
  • Josemon J, Espenson JH. Stereospecific rhenium catalyzed desulfurization of thiiranes. Chem Commun. 1999;1999:1003–1004.
  • Jun’ichi U, Yuhki K. An extremely mild desulfurization of thiiranes; an efficient transformation from geraniol to (+)- and (-)-linalool. Tetrahedron Lett. 1994;36:6697–6700.
  • Proulx G, Robert GB. Stereospecific heteroatom and hetero group transfer from oxiranes thiiranes, and aziridines by a simple alkyl tantalocene. J Am Chem Soc. 1994;116:7953–7954. doi: 10.1021/ja00096a085
  • Caló V, Lopez L, Nacci A, et al. Aminium salts induced desulfurization of allyl and diallyl thiiranes. synthesis of dienes and trienes. Tetrahedron. 1995;51:8935–8940. doi: 10.1016/0040-4020(95)00502-Y
  • Lutz E, Biellmann J-F. Mechanism of sulfur extrusion from thiirane. Tetrahedron Lett. 1985;26:2789–2792. doi: 10.1016/S0040-4039(00)94913-X
  • Reid AH, Shevlin PB, Webb TR, et al. Molybdenum atom desulfurizations of organosulfur compounds. J Org Chem. 1984;49:4728–4730. doi: 10.1021/jo00198a031
  • Vedejs E, Perry DA, Wilde RG. Characterization of monomeric thiopivalaldehyde. J Am Chem Soc. 1986;108:2985–2989. doi: 10.1021/ja00271a030
  • Masaki K, Kazuyuki M, Tsutomu M. Aminium radical salt catalyzed desulphurization of thiiranes: an efficient preparation of arylsubstituted olefins. Tetrahedron Lett. 1989;30:4129–4132. doi: 10.1016/S0040-4039(01)93904-8
  • Wang Z, Kuninobu Y, Kanai M. Molybdenum-mediated desulfurization of thiols and disulfides. Synlett. 2014;25:1869–1872. doi: 10.1055/s-0034-1378315
  • Tranmer GK, Tam W. Molybdenum-mediated cleavage reactions of isoxazoline rings fused in bicyclic frameworks. Org Lett. 2002;4:4101–4104. doi: 10.1021/ol026846k
  • Massa A, Acocella MR, De Rosa M, et al. Mo(CO)6-catalyzed oxidation of furan derivatives to E- and Z-enediones by cumyl hydroperoxide. Tetrahedron Lett. 2003;44:835–837. doi: 10.1016/S0040-4039(02)02636-9
  • Spencer J, Rathnam RP, Patel H, et al. Microwave mediated reduction of heterocycle and fluorine containing nitroaromatics with Mo(CO)6 and DBU. Tetrahedron. 2008;64:10195–10200. doi: 10.1016/j.tet.2008.08.036
  • Wu X, Mahalingam AK, Wan Y, et al. Fast microwave promoted palladium-catalyzed synthesis of phthalides from bromobenzyl alcohols utilizing DMF and Mo(CO)6 as carbon monoxide sources. Tetrahedron Lett. 2004;45:4635–4638. doi: 10.1016/j.tetlet.2004.04.110
  • Iyer S, Kulkarni GM. Mo(CO)6 mediated selective reduction of azides and nitro compounds to amines under neutral conditions. Synth Commun. 2004;34:721–725. doi: 10.1081/SCC-120027720
  • Patra A, Bandyopadhyay M, Mal D. Mo(CO)6-promoted facile deoxygenation of α,β-epoxy ketones and α,β-epoxy esters. Tetrahedron Lett. 2003;44:2355–2357. doi: 10.1016/S0040-4039(03)00231-4
  • Yoo BW, Song MS, Park MC. A facile and efficient deoxygenation of sulfoxides with Mo(CO)6. Bull Korean Chem Soc. 2007;28:171–172. doi: 10.5012/bkcs.2007.28.2.171
  • Yoo BW, Choi JW, Yoon CM. A facile and efficient deoxygenation of amine-N-oxides with Mo(CO)6. Tetrahedron Lett. 2006;47:125–126. doi: 10.1016/j.tetlet.2005.10.143
  • Iranpoor N, Kazemi F. Cerium(IV) catalysis: efficient conversion of epoxides to thiiranes. Synthesis. 1996;1996:821–822. doi: 10.1055/s-1996-4307
  • Klabund KJ. In Reactive intermediates; Vol. I; Abramovitch RA, editor; Chap. 2; New York: Academic Press; 1980.
  • Pouchert CJ, Behnke J, editors. The Aldrich Library of 13C and 1H FT-NMR spectra. Aldrich: Milwaukee; 1992.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.