RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2016; 48(18): 3087-3096
DOI: 10.1055/s-0035-1561629
DOI: 10.1055/s-0035-1561629
paper
Catalyst-Free, Regioselective Ring Opening of Donor–Acceptor Cyclopropanes: Synthesis of Functionalized Mono- and Disulfides
Weitere Informationen
Publikationsverlauf
Received: 24. Februar 2016
Accepted after revision: 04. April 2016
Publikationsdatum:
13. Mai 2016 (online)

Abstract
Interesting sulfur compounds such as monosulfides, symmetrical disulfides, unsymmetrical disulfides, and other 1,3-bifunctionalized compounds were synthesized using benzyltriethylammonium tetrathiomolybdate, [BnNEt3]2MoS4, as the sulfur transfer reagent via regioselective ring opening of donor–acceptor cyclopropanes without the addition of any catalyst.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1561629.
- Supporting Information
-
References
- 1 Cremlyn RJ. An Introduction to Organosulfur Chemistry . Wiley; Chichester: 1996
- 2a Fluharty AL In The Chemistry of the Thiol Group . Patai S. Wiley Interscience; New York: 1974. Part 2. 589
- 2b Trost BM, Keeley DE. J. Org. Chem. 1975; 40: 2013
- 2c Kumar A, Salunkhe RV, Rane RA, Dike SY. J. Chem. Soc., Chem. Commun. 1991; 485
- 3 Sevier CS, Kaiser CA. Nat. Rev. Mol. Cell Biol. 2002; 3: 836
- 4a Smith MB, March J. March’s Advanced Organic Chemistry . 6th ed. Wiley; Hoboken: 2007
- 4b Yin J, Pidegon C. Tetrahedron Lett. 1997; 38: 5953
- 5a Itoh T, Mase T. Org. Lett. 2004; 6: 4587
- 5b Bates CG, Gujadhur RK, Venkataraman D. Org. Lett. 2002; 4: 2803
- 5c Murata M, Buchwald SL. Tetrahedron 2004; 60: 7397
- 5d Li GY. Angew. Chem. Int. Ed. 2001; 40: 1513
- 5e Ogawa A, Ikeda T, Kimura K, Hirao T. J. Am. Chem. Soc. 1999; 121: 5108
- 6 Firouzabadi H, Iranpoor N, Jafarpour M, Ghaderi A. J. Mol. Catal. A: Chem. 2006; 249: 98
- 7 Chelucci G, Culeddu N, Saba A, Valenti R. Tetrahedron: Asymmetry 1999; 10: 3537
- 8a Wardell JL, Clarke PL. J. Organomet. Chem. 1971; 26: 345
- 8b Harpp DN, Friedlander BT, Larsen C, Steliou K, Stockton A. J. Org. Chem. 1978; 43: 3481
- 8c Brown C, Evans GR. Tetrahedron Lett. 1996; 37: 9101
- 8d Capozzi G, Capperucci A, Degl’Innocenti A, Del Duce R, Menichetti S. Tetrahedron Lett. 1989; 30: 2995
- 8e Rajca A, Wiessler M. Tetrahedron Lett. 1990; 31: 6075
- 8f Hiver P, Dicko A, Paquer D. Tetrahedron Lett. 1994; 35: 9569
- 8g Harpp DH, Ash DK, Back TG, Gleason JG, Orwig BA, VanHorn WF, Snyder JP. Tetrahedron Lett. 1970; 11: 3551
- 8h Boustang KS, Sullivan AB. Tetrahedron Lett. 1970; 3547
- 9a Parker AJ, Kharasch N. Chem. Rev. 1959; 59: 583
- 9b Gorin G, Dougherty G, Tobolsky AV. J. Am. Chem. Soc. 1949; 71: 3551
- 10a Blanchard LA, Schneider JA. J. Org. Chem. 1986; 51: 1372
- 10b Stewart JM, Westberg HH. J. Org. Chem. 1965; 30: 1951
- 10c Wurz RP, Carette AB. Org. Lett. 2005; 7: 2313
- 10d Lifchits O, Alberico D, Zakharian I, Charette AB. J. Org. Chem. 2008; 73: 6838
- 10e Lebold TP, Kerr MA. Org. Lett. 2009; 11: 4354
- 10f Lifchits O, Charette AB. Org. Lett. 2008; 10: 2809
- 10g Danishefsky S. Acc. Chem. Res. 1979; 12: 66
- 10h Dolfini JE, Menich K, Corliss P. Tetrahedron Lett. 1966; 37: 4421
- 10i Reissig H.-U, Zimmer R. Chem. Rev. 2003; 103: 1151
- 10j Schneider TF, Kaschel J, Werz DB. Angew. Chem. Int. Ed. 2014; 53: 5504
- 10k Yu M, Pagenkopf BL. Tetrahedron 2003; 59: 2765
- 10l Garve LK. B, Pawliczek M, Wallbaum J, Jones PG, Werz DB. Chem. Eur. J. 2016; 22: 521
- 11 Jonsson SY, Lofstrom CM. G, Backvall JE. J. Org. Chem. 2000; 65: 8454
- 12 Gopinath P, Chandrasekaran S. J. Org. Chem. 2011; 76: 700
- 13 Gopinath P, Chandrakala RN, Chandrasekaran S. Synthesis 2015; 47: 1488
- 14 Prabhu KR, Devan N, Chandrasekaran S. Synlett 2002; 1762
- 15a Pan WH, Harmer MA, Halbert TR, Stiefel EI. J. Am. Chem. Soc. 1984; 106: 459
- 15b Prabhu KR, Sivanand P, Chandrasekaran S. Angew. Chem. Int. Ed. 2000; 39: 4316
- 16 Sureshkumar D, Ganesh V, Vidyarini RS, Chandrasekaran S. J. Org. Chem. 2009; 74: 7958
- 17 Ramesha AR, Chandrasekaran S. Synth. Commun. 1992; 22: 3277
- 18a Froyen P. Phosphorus Sulfur and Silicon 1994; 89: 57
- 18b Froyen P. Phosphorus Sulfur and Silicon 1994; 91: 145
- 18c Froyen P. Synth. Commun. 1995; 25: 959
- 18d Sucheta K, Reddy GS. R, Ravi D, Rama Rao N. Tetrahedron Lett. 1994; 35: 4415
- 19a Gopinath P, Vidyarini RS, Chandrasekaran S. J. Org. Chem. 2009; 74: 6291
- 19b Gopinath P, Vidyarini RS, Chandrasekaran S. Eur. J. Org. Chem. 2009; 6043
- 19c Gopinath P, Debasree C, Vidyarini RS, Chandrasekaran S. Tetrahedron 2010; 66: 7001
- 20 Wurz RP, Charette AB. Org. Lett. 2003; 5: 2327
- 21 O’Bannon PE, Dailey WP. J. Org. Chem. 1990; 55: 353
- 22 Pryor WA, Church DF, Govindan CK, Crank G. J. Org. Chem. 1982; 47: 156
- 23 Krishnamurthy S, Aimino D. J. Org. Chem. 1989; 54: 4458
- 24 Oae S, Yamada N, Fujimori K, Kikuchi O. Bull. Chem. Soc. Jpn. 1983; 56: 248
- 25 Xiao H, Chen J, Liu M, Wu H, Ding J. Phosphorus Sulfur and Silicon 2009; 184: 2553
- 26 Zeynizadeh B. J. Chem. Res., Synop. 2002; 564