Use of electrochemical methods as an alternative to tin reagents for the reduction of vinyl halides in inositol synthons

Journal of Organic Chemistry

Volumn 64, Issue 13, 1999, Pages 4909-4913

  Hudlicky, Tomas ^a   Claeboe, Christopher D ^a   Brammer Jr , Larry E ^a   Koroniak, Lukasz ^a,b   Butora, Gabor ^a   Ghiviriga, Ion ^a  

^a University of Florida ^*  (United States)

^b ADAM MICKIEWICZ UNIVERSITY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 EPOXY 3 BUTENE; ALKENE; ALLYL ALCOHOL; INOSITOL; TIN; VINYL DERIVATIVE;

ARTICLE; CHEMICAL REACTION; DEHALOGENATION; ELECTRIC POTENTIAL; ELECTROCHEMISTRY; REDUCTION; SYNTHESIS;

EID: 0033603621     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990382v     Document Type: Article

References (34)

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2. For comprehensive reviews of arene cis-diol chemistry see: (a) Brown, S. M.; Hudlicky, T. In Organic Synthesis: Theory and Applications; Hudlicky, T., Ed.; JAI Press: Greenwich, CT, 1993; Vol. 2, pp 113-176. (b) Widdowson, D. A.; Ribbons, D. W.; Thomas, S. D. Janssen Chim. Acta 1990, 8, 3. (c) Carless, H. A. J. Tetrahedron: Asymmetry 1992,3, 795. (d) Hudlicky, T.; Reed, J. W. In Advances in Asymmetric Synthesis; Hassner, A., Ed.; JAI Press: Greenwich, CT, 1995; p 271. (e) Hudlicky, T. In Green Chemistry: Designing Chemistry for the Environment; Anastas, P. T., Williamson, T., Eds.; ACS Symposium Series 626, American Chemical Society: Washington, DC., 1996; Chapter 14. (f) Hudlicky, T.; Thorpe, A. J. J. Chem. Soc., Chem. Commun. 1996, 1993. (g) Hudlicky, T. Chem. Rev. 1996, 96, 3. (h) Hudlicky, T.; Entwistle, D. A.; Pitzer, K. K.; Thorpe, A. J. Chem. Rev. 1996, 96, 1195. (i) Grund, A. D. SIM News 1995, 45, 59. (j) Boyd, D. R. Nat. Prod. Rep. 1998, 309. (j) Hudlicky, T.; Gonzalez, D.; Gibson, D. T. Aldrichimica Acta 1999, in press.
3. For comprehensive reviews of arene cis-diol chemistry see: (a) Brown, S. M.; Hudlicky, T. In Organic Synthesis: Theory and Applications; Hudlicky, T., Ed.; JAI Press: Greenwich, CT, 1993; Vol. 2, pp 113-176. (b) Widdowson, D. A.; Ribbons, D. W.; Thomas, S. D. Janssen Chim. Acta 1990, 8, 3. (c) Carless, H. A. J. Tetrahedron: Asymmetry 1992,3, 795. (d) Hudlicky, T.; Reed, J. W. In Advances in Asymmetric Synthesis; Hassner, A., Ed.; JAI Press: Greenwich, CT, 1995; p 271. (e) Hudlicky, T. In Green Chemistry: Designing Chemistry for the Environment; Anastas, P. T., Williamson, T., Eds.; ACS Symposium Series 626, American Chemical Society: Washington, DC., 1996; Chapter 14. (f) Hudlicky, T.; Thorpe, A. J. J. Chem. Soc., Chem. Commun. 1996, 1993. (g) Hudlicky, T. Chem. Rev. 1996, 96, 3. (h) Hudlicky, T.; Entwistle, D. A.; Pitzer, K. K.; Thorpe, A. J. Chem. Rev. 1996, 96, 1195. (i) Grund, A. D. SIM News 1995, 45, 59. (j) Boyd, D. R. Nat. Prod. Rep. 1998, 309. (j) Hudlicky, T.; Gonzalez, D.; Gibson, D. T. Aldrichimica Acta 1999, in press.
4. For comprehensive reviews of arene cis-diol chemistry see: (a) Brown, S. M.; Hudlicky, T. In Organic Synthesis: Theory and Applications; Hudlicky, T., Ed.; JAI Press: Greenwich, CT, 1993; Vol. 2, pp 113-176. (b) Widdowson, D. A.; Ribbons, D. W.; Thomas, S. D. Janssen Chim. Acta 1990, 8, 3. (c) Carless, H. A. J. Tetrahedron: Asymmetry 1992,3, 795. (d) Hudlicky, T.; Reed, J. W. In Advances in Asymmetric Synthesis; Hassner, A., Ed.; JAI Press: Greenwich, CT, 1995; p 271. (e) Hudlicky, T. In Green Chemistry: Designing Chemistry for the Environment; Anastas, P. T., Williamson, T., Eds.; ACS Symposium Series 626, American Chemical Society: Washington, DC., 1996; Chapter 14. (f) Hudlicky, T.; Thorpe, A. J. J. Chem. Soc., Chem. Commun. 1996, 1993. (g) Hudlicky, T. Chem. Rev. 1996, 96, 3. (h) Hudlicky, T.; Entwistle, D. A.; Pitzer, K. K.; Thorpe, A. J. Chem. Rev. 1996, 96, 1195. (i) Grund, A. D. SIM News 1995, 45, 59. (j) Boyd, D. R. Nat. Prod. Rep. 1998, 309. (j) Hudlicky, T.; Gonzalez, D.; Gibson, D. T. Aldrichimica Acta 1999, in press.
5. For comprehensive reviews of arene cis-diol chemistry see: (a) Brown, S. M.; Hudlicky, T. In Organic Synthesis: Theory and Applications; Hudlicky, T., Ed.; JAI Press: Greenwich, CT, 1993; Vol. 2, pp 113-176. (b) Widdowson, D. A.; Ribbons, D. W.; Thomas, S. D. Janssen Chim. Acta 1990, 8, 3. (c) Carless, H. A. J. Tetrahedron: Asymmetry 1992,3, 795. (d) Hudlicky, T.; Reed, J. W. In Advances in Asymmetric Synthesis; Hassner, A., Ed.; JAI Press: Greenwich, CT, 1995; p 271. (e) Hudlicky, T. In Green Chemistry: Designing Chemistry for the Environment; Anastas, P. T., Williamson, T., Eds.; ACS Symposium Series 626, American Chemical Society: Washington, DC., 1996; Chapter 14. (f) Hudlicky, T.; Thorpe, A. J. J. Chem. Soc., Chem. Commun. 1996, 1993. (g) Hudlicky, T. Chem. Rev. 1996, 96, 3. (h) Hudlicky, T.; Entwistle, D. A.; Pitzer, K. K.; Thorpe, A. J. Chem. Rev. 1996, 96, 1195. (i) Grund, A. D. SIM News 1995, 45, 59. (j) Boyd, D. R. Nat. Prod. Rep. 1998, 309. (j) Hudlicky, T.; Gonzalez, D.; Gibson, D. T. Aldrichimica Acta 1999, in press.
6. For comprehensive reviews of arene cis-diol chemistry see: (a) Brown, S. M.; Hudlicky, T. In Organic Synthesis: Theory and Applications; Hudlicky, T., Ed.; JAI Press: Greenwich, CT, 1993; Vol. 2, pp 113-176. (b) Widdowson, D. A.; Ribbons, D. W.; Thomas, S. D. Janssen Chim. Acta 1990, 8, 3. (c) Carless, H. A. J. Tetrahedron: Asymmetry 1992,3, 795. (d) Hudlicky, T.; Reed, J. W. In Advances in Asymmetric Synthesis; Hassner, A., Ed.; JAI Press: Greenwich, CT, 1995; p 271. (e) Hudlicky, T. In Green Chemistry: Designing Chemistry for the Environment; Anastas, P. T., Williamson, T., Eds.; ACS Symposium Series 626, American Chemical Society: Washington, DC., 1996; Chapter 14. (f) Hudlicky, T.; Thorpe, A. J. J. Chem. Soc., Chem. Commun. 1996, 1993. (g) Hudlicky, T. Chem. Rev. 1996, 96, 3. (h) Hudlicky, T.; Entwistle, D. A.; Pitzer, K. K.; Thorpe, A. J. Chem. Rev. 1996, 96, 1195. (i) Grund, A. D. SIM News 1995, 45, 59. (j) Boyd, D. R. Nat. Prod. Rep. 1998, 309. (j) Hudlicky, T.; Gonzalez, D.; Gibson, D. T. Aldrichimica Acta 1999, in press.
7. For comprehensive reviews of arene cis-diol chemistry see: (a) Brown, S. M.; Hudlicky, T. In Organic Synthesis: Theory and Applications; Hudlicky, T., Ed.; JAI Press: Greenwich, CT, 1993; Vol. 2, pp 113-176. (b) Widdowson, D. A.; Ribbons, D. W.; Thomas, S. D. Janssen Chim. Acta 1990, 8, 3. (c) Carless, H. A. J. Tetrahedron: Asymmetry 1992,3, 795. (d) Hudlicky, T.; Reed, J. W. In Advances in Asymmetric Synthesis; Hassner, A., Ed.; JAI Press: Greenwich, CT, 1995; p 271. (e) Hudlicky, T. In Green Chemistry: Designing Chemistry for the Environment; Anastas, P. T., Williamson, T., Eds.; ACS Symposium Series 626, American Chemical Society: Washington, DC., 1996; Chapter 14. (f) Hudlicky, T.; Thorpe, A. J. J. Chem. Soc., Chem. Commun. 1996, 1993. (g) Hudlicky, T. Chem. Rev. 1996, 96, 3. (h) Hudlicky, T.; Entwistle, D. A.; Pitzer, K. K.; Thorpe, A. J. Chem. Rev. 1996, 96, 1195. (i) Grund, A. D. SIM News 1995, 45, 59. (j) Boyd, D. R. Nat. Prod. Rep. 1998, 309. (j) Hudlicky, T.; Gonzalez, D.; Gibson, D. T. Aldrichimica Acta 1999, in press.
8. For comprehensive reviews of arene cis-diol chemistry see: (a) Brown, S. M.; Hudlicky, T. In Organic Synthesis: Theory and Applications; Hudlicky, T., Ed.; JAI Press: Greenwich, CT, 1993; Vol. 2, pp 113-176. (b) Widdowson, D. A.; Ribbons, D. W.; Thomas, S. D. Janssen Chim. Acta 1990, 8, 3. (c) Carless, H. A. J. Tetrahedron: Asymmetry 1992,3, 795. (d) Hudlicky, T.; Reed, J. W. In Advances in Asymmetric Synthesis; Hassner, A., Ed.; JAI Press: Greenwich, CT, 1995; p 271. (e) Hudlicky, T. In Green Chemistry: Designing Chemistry for the Environment; Anastas, P. T., Williamson, T., Eds.; ACS Symposium Series 626, American Chemical Society: Washington, DC., 1996; Chapter 14. (f) Hudlicky, T.; Thorpe, A. J. J. Chem. Soc., Chem. Commun. 1996, 1993. (g) Hudlicky, T. Chem. Rev. 1996, 96, 3. (h) Hudlicky, T.; Entwistle, D. A.; Pitzer, K. K.; Thorpe, A. J. Chem. Rev. 1996, 96, 1195. (i) Grund, A. D. SIM News 1995, 45, 59. (j) Boyd, D. R. Nat. Prod. Rep. 1998, 309. (j) Hudlicky, T.; Gonzalez, D.; Gibson, D. T. Aldrichimica Acta 1999, in press.
9. For comprehensive reviews of arene cis-diol chemistry see: (a) Brown, S. M.; Hudlicky, T. In Organic Synthesis: Theory and Applications; Hudlicky, T., Ed.; JAI Press: Greenwich, CT, 1993; Vol. 2, pp 113-176. (b) Widdowson, D. A.; Ribbons, D. W.; Thomas, S. D. Janssen Chim. Acta 1990, 8, 3. (c) Carless, H. A. J. Tetrahedron: Asymmetry 1992,3, 795. (d) Hudlicky, T.; Reed, J. W. In Advances in Asymmetric Synthesis; Hassner, A., Ed.; JAI Press: Greenwich, CT, 1995; p 271. (e) Hudlicky, T. In Green Chemistry: Designing Chemistry for the Environment; Anastas, P. T., Williamson, T., Eds.; ACS Symposium Series 626, American Chemical Society: Washington, DC., 1996; Chapter 14. (f) Hudlicky, T.; Thorpe, A. J. J. Chem. Soc., Chem. Commun. 1996, 1993. (g) Hudlicky, T. Chem. Rev. 1996, 96, 3. (h) Hudlicky, T.; Entwistle, D. A.; Pitzer, K. K.; Thorpe, A. J. Chem. Rev. 1996, 96, 1195. (i) Grund, A. D. SIM News 1995, 45, 59. (j) Boyd, D. R. Nat. Prod. Rep. 1998, 309. (j) Hudlicky, T.; Gonzalez, D.; Gibson, D. T. Aldrichimica Acta 1999, in press.
10. For comprehensive reviews of arene cis-diol chemistry see: (a) Brown, S. M.; Hudlicky, T. In Organic Synthesis: Theory and Applications; Hudlicky, T., Ed.; JAI Press: Greenwich, CT, 1993; Vol. 2, pp 113-176. (b) Widdowson, D. A.; Ribbons, D. W.; Thomas, S. D. Janssen Chim. Acta 1990, 8, 3. (c) Carless, H. A. J. Tetrahedron: Asymmetry 1992,3, 795. (d) Hudlicky, T.; Reed, J. W. In Advances in Asymmetric Synthesis; Hassner, A., Ed.; JAI Press: Greenwich, CT, 1995; p 271. (e) Hudlicky, T. In Green Chemistry: Designing Chemistry for the Environment; Anastas, P. T., Williamson, T., Eds.; ACS Symposium Series 626, American Chemical Society: Washington, DC., 1996; Chapter 14. (f) Hudlicky, T.; Thorpe, A. J. J. Chem. Soc., Chem. Commun. 1996, 1993. (g) Hudlicky, T. Chem. Rev. 1996, 96, 3. (h) Hudlicky, T.; Entwistle, D. A.; Pitzer, K. K.; Thorpe, A. J. Chem. Rev. 1996, 96, 1195. (i) Grund, A. D. SIM News 1995, 45, 59. (j) Boyd, D. R. Nat. Prod. Rep. 1998, 309. (j) Hudlicky, T.; Gonzalez, D.; Gibson, D. T. Aldrichimica Acta 1999, in press.
11. For comprehensive reviews of arene cis-diol chemistry see: (a) Brown, S. M.; Hudlicky, T. In Organic Synthesis: Theory and Applications; Hudlicky, T., Ed.; JAI Press: Greenwich, CT, 1993; Vol. 2, pp 113-176. (b) Widdowson, D. A.; Ribbons, D. W.; Thomas, S. D. Janssen Chim. Acta 1990, 8, 3. (c) Carless, H. A. J. Tetrahedron: Asymmetry 1992,3, 795. (d) Hudlicky, T.; Reed, J. W. In Advances in Asymmetric Synthesis; Hassner, A., Ed.; JAI Press: Greenwich, CT, 1995; p 271. (e) Hudlicky, T. In Green Chemistry: Designing Chemistry for the Environment; Anastas, P. T., Williamson, T., Eds.; ACS Symposium Series 626, American Chemical Society: Washington, DC., 1996; Chapter 14. (f) Hudlicky, T.; Thorpe, A. J. J. Chem. Soc., Chem. Commun. 1996, 1993. (g) Hudlicky, T. Chem. Rev. 1996, 96, 3. (h) Hudlicky, T.; Entwistle, D. A.; Pitzer, K. K.; Thorpe, A. J. Chem. Rev. 1996, 96, 1195. (i) Grund, A. D. SIM News 1995, 45, 59. (j) Boyd, D. R. Nat. Prod. Rep. 1998, 309. (j) Hudlicky, T.; Gonzalez, D.; Gibson, D. T. Aldrichimica Acta 1999, in press.
12. For reviews on electrochemical methods of synthesis, see: (a) Lund, H.; Baizer, M. M. Organic Electrochemistry: An Introduction and a Guide; Marcel Dekker: New York, 1991. (b) Volke, J.; Liska, F. In Electrochemistry in Organic Synthesis; Springer-Verlag: New York, 1994; pp 1-44, 90. (c) Utley, J. J. Chem. Soc. Rev. 1997, 26, 157. (d) Saiganesh, R.; Balasubramanian, K. K.; Venkatachalam, C. S. J. Electroanal. Chem. 1989, 262, 221. For recent applications, see: (e) Rossen, K.; Volante, R. P.; Reider, P. J. Tetrahedron Lett. 1997, 38, 777. (f) Frey, D. A.; Wu, N.; Moeller, K. D. Tetrahedron Lett. 1996, 37, 8317. (g) Moeller, K. D. Topics in Current Chemistry; Springer- Verlag: Berlin, 1997; Vol. 185, p 50.
13. For reviews on electrochemical methods of synthesis, see: (a) Lund, H.; Baizer, M. M. Organic Electrochemistry: An Introduction and a Guide; Marcel Dekker: New York, 1991. (b) Volke, J.; Liska, F. In Electrochemistry in Organic Synthesis; Springer-Verlag: New York, 1994; pp 1-44, 90. (c) Utley, J. J. Chem. Soc. Rev. 1997, 26, 157. (d) Saiganesh, R.; Balasubramanian, K. K.; Venkatachalam, C. S. J. Electroanal. Chem. 1989, 262, 221. For recent applications, see: (e) Rossen, K.; Volante, R. P.; Reider, P. J. Tetrahedron Lett. 1997, 38, 777. (f) Frey, D. A.; Wu, N.; Moeller, K. D. Tetrahedron Lett. 1996, 37, 8317. (g) Moeller, K. D. Topics in Current Chemistry; Springer- Verlag: Berlin, 1997; Vol. 185, p 50.
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