A novel domino reaction: Cyclization of alkynyl sulfides by reaction with IPy2BF4

Angewandte Chemie - International Edition

Volumn 37, Issue 22, 1998, Pages 3136-3139

  Barluenga, José ^a   Romanelli, Gustavo P ^a   Alvarez García, Lorenzo J ^a   Llorente, Isidro ^a   González, José M ^a   García Rodríguez, Esther ^a   García Granda, Santiago ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

Alkynes; Cyclizations; Domino reactions; Heterocycles

Indexed keywords

ALKYNE DERIVATIVE; ALKYNYL GROUP; SULFIDE;

ARTICLE; CHEMICAL BINDING; CYCLIZATION; MOLECULAR INTERACTION; STOICHIOMETRY;

EID: 0032484054     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19981204)37:22<3136::AID-ANIE3136>3.0.CO;2-O     Document Type: Article

References (42)

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18. Acetylenic sulfides are useful compounds in organic synthesis: S. Y. Radchenko, A. A. Petrov, Russ. Chem. Rev. (Engl. Transl.) 1989, 58, 948-966; P. Nebois, N. Kann, A. E. Greene, J. Org. Chem. 1995, 60, 7690-7692; H. Ishitani, S. Nagayama, S. Kobayashi, J. Org. Chem. 1996, 61, 1902-1903.
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26. 1H NMR data, representative UV/Vis, IR, and MS data and elemental analyses, see the supporting information.
27. The structures of 2c, 2d, and 4 were determined by X-ray analysis. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-102304 (4), CCDC-102305 (2c), and CCDC-102306 (2d). Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: (+44) 1223-336-033; e-mail:deposil@ccdc.cam.ac.uk).
28. 3): δ = 95.8 (CI).
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30. Review: K. P. Meurer, F. Vögtle, Top. Curr. Chem. 1985, 127, 1-76; see also: A. Beck, R. Gompper, K. Polborn, H.-U. Wagner, Angew. Chem. 1993, 105, 1424-1427; Angew. Chem. Int. Ed. Engl. 1993, 32, 1352-1354; B. L. Feringa, N. P. M. Huck, A. M. Schoevaars, Adv. Mater. 1996, 8, 681-684.
31. Review: K. P. Meurer, F. Vögtle, Top. Curr. Chem. 1985, 127, 1-76; see also: A. Beck, R. Gompper, K. Polborn, H.-U. Wagner, Angew. Chem. 1993, 105, 1424-1427; Angew. Chem. Int. Ed. Engl. 1993, 32, 1352-1354; B. L. Feringa, N. P. M. Huck, A. M. Schoevaars, Adv. Mater. 1996, 8, 681-684.
32. Review: K. P. Meurer, F. Vögtle, Top. Curr. Chem. 1985, 127, 1-76; see also: A. Beck, R. Gompper, K. Polborn, H.-U. Wagner, Angew. Chem. 1993, 105, 1424-1427; Angew. Chem. Int. Ed. Engl. 1993, 32, 1352-1354; B. L. Feringa, N. P. M. Huck, A. M. Schoevaars, Adv. Mater. 1996, 8, 681-684.
33. 4, see J. Barluenga, P. J. Campos, F. López, I. Llorente, M. A. Rodríguez, Tetrahedron Lett. 1990, 31, 7375-7378.
34. For the directive effect of sulfur on electrophilic addition to acetylene, see G. Modena, U. Tonellato, Adv. Phys. Org. Chem. 1971, 9, 185.
35. Alternative radical pathways cannot be ruled out, but should occur in an exo-exo mode (according to S. Caddick, C. L. Shering, S. N. Wadman, Chem. Commun. 1997, 171-172). No evidence for significant sulfur oxidation was found during the reaction. Moreover, the addition of BHT to the reaction mixture did not affect the cyclization.
36. M. Hanack, Angew. Chem. 1978, 90, 346-354; Angew. Chem. Int. Ed. Engl. 1978, 17, 333-341.
37. M. Hanack, Angew. Chem. 1978, 90, 346-354; Angew. Chem. Int. Ed. Engl. 1978, 17, 333-341.
38. Compound 9 and related structures based on alkene linkers could be of interest for second-order nonlinear optics: S. R. Marder, J. W. Perry, Adv. Mater. 1993, 5, 804-815; M. S. Wong, C. Bosshard, F. Pan, P. Günter, Adv. Mater. 1996, 8, 677-680; M. S. Wong, C. Bosshard, P. Günter, Adv. Mater. 1997, 9, 837-842. Furthermore, 10, or related compounds from the coupling of 7 with diiodides 2f or 2g, could be precursors for new poly(aryleneethynylene) (PAE) polymers containing 2,5-thienylene units: T. Yamamoto, K. Honda, N. Ooba, S. Tomaru, Macromolecules 1998, 31, 7-14. Angew. Client. Int. Ed. 1998, 37, No. 22
39. Compound 9 and related structures based on alkene linkers could be of interest for second-order nonlinear optics: S. R. Marder, J. W. Perry, Adv. Mater. 1993, 5, 804-815; M. S. Wong, C. Bosshard, F. Pan, P. Günter, Adv. Mater. 1996, 8, 677-680; M. S. Wong, C. Bosshard, P. Günter, Adv. Mater. 1997, 9, 837-842. Furthermore, 10, or related compounds from the coupling of 7 with diiodides 2f or 2g, could be precursors for new poly(aryleneethynylene) (PAE) polymers containing 2,5-thienylene units: T. Yamamoto, K. Honda, N. Ooba, S. Tomaru, Macromolecules 1998, 31, 7-14. Angew. Client. Int. Ed. 1998, 37, No. 22
40. Compound 9 and related structures based on alkene linkers could be of interest for second-order nonlinear optics: S. R. Marder, J. W. Perry, Adv. Mater. 1993, 5, 804-815; M. S. Wong, C. Bosshard, F. Pan, P. Günter, Adv. Mater. 1996, 8, 677-680; M. S. Wong, C. Bosshard, P. Günter, Adv. Mater. 1997, 9, 837-842. Furthermore, 10, or related compounds from the coupling of 7 with diiodides 2f or 2g, could be precursors for new poly(aryleneethynylene) (PAE) polymers containing 2,5-thienylene units: T. Yamamoto, K. Honda, N. Ooba, S. Tomaru, Macromolecules 1998, 31, 7-14. Angew. Client. Int. Ed. 1998, 37, No. 22
41. Compound 9 and related structures based on alkene linkers could be of interest for second-order nonlinear optics: S. R. Marder, J. W. Perry, Adv. Mater. 1993, 5, 804-815; M. S. Wong, C. Bosshard, F. Pan, P. Günter, Adv. Mater. 1996, 8, 677-680; M. S. Wong, C. Bosshard, P. Günter, Adv. Mater. 1997, 9, 837-842. Furthermore, 10, or related compounds from the coupling of 7 with diiodides 2f or 2g, could be precursors for new poly(aryleneethynylene) (PAE) polymers containing 2,5-thienylene units: T. Yamamoto, K. Honda, N. Ooba, S. Tomaru, Macromolecules 1998, 31, 7-14. Angew. Client. Int. Ed. 1998, 37, No. 22
42. Compound 9 and related structures based on alkene linkers could be of interest for second-order nonlinear optics: S. R. Marder, J. W. Perry, Adv. Mater. 1993, 5, 804-815; M. S. Wong, C. Bosshard, F. Pan, P. Günter, Adv. Mater. 1996, 8, 677-680; M. S. Wong, C. Bosshard, P. Günter, Adv. Mater. 1997, 9, 837-842. Furthermore, 10, or related compounds from the coupling of 7 with diiodides 2f or 2g, could be precursors for new poly(aryleneethynylene) (PAE) polymers containing 2,5-thienylene units: T. Yamamoto, K. Honda, N. Ooba, S. Tomaru, Macromolecules 1998, 31, 7-14. Angew. Client. Int. Ed. 1998, 37, No. 22