Ethynyltributyltin - A synthetic equivalent for acetylene, aryl, acyl and halogeno alkynes in [4+2] cycloadditions

Tetrahedron Letters

Volumn 39, Issue 17, 1998, Pages 2549-2552

  Sauer, Jürgen ^a   Heldmann, Dieter K ^a  

^a UNIVERSITY OF REGENSBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ETHYNYLTRIBUTYLTIN; ORGANOTIN COMPOUND; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CATALYSIS; HALOGENATION; PROTON TRANSPORT; REACTION ANALYSIS; SYNTHESIS;

EID: 0032559958     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00343-8     Document Type: Article

References (14)

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2. 2. Heldmann, D.K.; Sauer, J. Tetrahedron Lett. 1997, 38, 5791-5794.
3. 3. Neunhoeffer, H.; 1,2,4-Triazines and their Benzo Derivates. In Comprehensive Heterocyclic Chemistry II; Pergamon Press: Oxford, 1996; Vol. 6, pp. 507-574.
4. 4 a) Balcar, J.; Chrisam, G.; Huber, F.X.; Sauer, J. Tetrahedron Lett. 1983, 24, 1481-1484.
5. b) Sauer, J.; 1,2,4,5-Tetrazines. In Comprehensive Heterocyclic Chemistry II; Pergamon Press: Oxford, 1996; Vol. 6, pp. 901-955.
6. 5. Goeckel, U.; Hartmannsgruber, U., Steigel, A.; Sauer, J. Tetrahedron Lett. 1980, 21, 595-598.
7. 2Sn (502.3): calcd. C 59.78, H 7.43, N 2.79; found C 59.96, H 7.09, N 3.49. - 3b was also characterized by all analytical methods.
8. 7. Sauer, J.; Heldmann D.K.; Tetrahedron 1998, 54, 4297-4312.
9. 8. a) Fukui, K. Fortsch. Chem. Forsch. 1970, 18, 1-85.
10. b) Sauer, J.; Sustmann, R.; Angew. Chem. 1980, 92, 773-802; Angew. Chem. Int. Ed. Engl. 1980, 19, 779-807.
11. b) Sauer, J.; Sustmann, R.; Angew. Chem. 1980, 92, 773-802; Angew. Chem. Int. Ed. Engl. 1980, 19, 779-807.
12. 3 (1.5 ml) was added and the flask closed loosely with a stopper. The reaction mixture was heated at 65°C (bath temperature) for the time indicated in table 1. Precipitated palladium (not always the case) was filtered off, the reaction mixture concentrated under reduced pressure, purified by fcc (petroleum ether 40/60 : ethyl acetate) and recrystallized (7a-c: cyclohexane : ethyl acetate; 7d-e: petroleum ether 40/60). Analytical and spectroscopic data for compounds 4-7 are in full accordance with those of the proposed structures. For details see the forthcoming Ph. D. thesis of Dieter Heldmann, University of Regensburg, 1998
13. 10. Stille, J.K. Angew. Chem. 1986, 98, 504-519; Angew. Chem. Int. Ed. Engl. 1986, 25, 508-523.
14. 10. Stille, J.K. Angew. Chem. 1986, 98, 504-519; Angew. Chem. Int. Ed. Engl. 1986, 25, 508-523.