A one-pot procedure for the synthesis of alkynes and bromoalkynes from aldehydes

Tetrahedron Letters

Volumn 40, Issue 49, 1999, Pages 8575-8578

  Michel, Patrick ^a   Gennet, Dominique ^a   Rassat, André ^a  

^a ECOLE NORMALE SUPÉRIEURE   (France)

Author keywords

Alkynes; Bromoalkynes; Dibromomethyltriphenylphosphonium bromide; Ylides

Indexed keywords

ALDEHYDE; ALKYNE DERIVATIVE; METHYLTRIPHENYLPHOSPHONIUM;

ARTICLE; CHEMICAL MODIFICATION; POLYMERIZATION; SYNTHESIS;

EID: 0033521149     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01830-4     Document Type: Article

References (12)

1. Corey, E. J.; Fuchs, P. L. Tetrahedron Lett. 1972, 3769-3772.
2. Ramirez, F.; Desai, N. B.; McKelvie, N. J. Am. Chem. Soc. 1962, 84, 1745-1747.
3. This ylide was also prepared from bromoform using Speziale's method. In our hands and contrary to what was observed with a black THF solution was obtained. Moreover, even with two equivalents of reagent, some starting material was still present, (a) Speziale, A. J.; Marco, G. J.; Ratts, K. W. J. Am. Chem. Soc. 1960, 82, 1260.
4. (b) Speziale, A. J.; Ratts, K. W. J. Am. Chem. Soc. 1962, 84, 854-859.
5. (c) Raulet, C.; Levas, E. Bull. Soc. Chim. Fr. 1971, 2598-2606.
6. (d) McIntosh M. C.; Weinreb, S. M. J. Org. Chem. 1991, 56, 5010-5012.
7. (a) Ramirez, F.; McKelvie, N. J. Am. Chem. Soc. 1957, 79, 5829-5830.
8. (b) Wolkoff, P. Can. J. Chem. 1975, 53, 1333-1335.
9. Enynes cannot be obtained from α,β-unsaturated aldehydes when dimethyl-1-diazo-2-oxopropylphosphonate is used: Müller, S.; Liepold, B.; Roth, G. J.; Bestmann, H. J. Synlett 1996, 521-522.
10. A conversion of a dibromoalkene to the bromoalkyne by t-BuOK has been reported: de Meijere, A.; Kozhushkov, S.; Haumann, T.; Boese, R.; Puls, C.; Cooney, M. J.; Scott, L. T. Chem. Eur. J. 1995, 1, 124-131.
11. A general method for the preparation of the analogous iodoalkynes is described in the accompanying communication: Michel, P.; Rassat, A. Tetrahedron Lett. 1999, 40, 8579-8581.
12. 3, 50 MHz): 23.8, 25.7, 32.0, 52.0, 60.2, 62.2, 80.0, 82.7, 108.5, 126.6, 128.0, 129.0, 139.0, 149.1.