A one-pot procedure for the synthesis of iodoalkynes from aldehydes

Tetrahedron Letters

Volumn 40, Issue 49, 1999, Pages 8579-8581

  Michel, Patrick ^a   Rassat, André ^a  

^a ECOLE NORMALE SUPÉRIEURE   (France)

Author keywords

Alkyne; Diiodomethyltriphenylphosphorane; Iodoalkyne; Ylides

Indexed keywords

ALDEHYDE; ALKYNE DERIVATIVE; IODOFORM; PHOSPHINE DERIVATIVE; PHOSPHORANE DERIVATIVE;

ARTICLE; METHODOLOGY; REACTION ANALYSIS; SYNTHESIS;

EID: 0033521150     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01831-6     Document Type: Article

References (15)

1. Preceeding communication: Michel, P.; Gennet, D.; Rassat, A. Tetrahedron Lett. 1999, 40, 8575-8578.
2. 2: Takai, K.; Kuroda, T.; Nakatsukasa, S.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1985, 26, 3769-3772, or the preparation of cisiodoaalkenes: Zweifel, G.; Arzoumanian, H. J. Am. Chem. Soc. 1967, 89, 5086-5088.
3. 2: Takai, K.;Kuroda, T.; Nakatsukasa, S.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1985, 26, 3769-3772, or the preparation of cis iodoaalkenes: Zweifel, G.; Arzoumanian, H. J. Am. Chem. Soc. 1967, 89, 5086-5088.
4. (a) Gavina, F.; Luis, S. V.; Ferrer, P.; Costero, A. M.; Marco, J. A. J. Chem. Soc., Chem. Commun. 1985, 296-297.
5. (b) Gavina, F.; Luis, S. V.; Ferrer, P.; Costero, A. M.; Marco, J. A. J. Chem. Res. 1986, 330-331.
6. (c) Gavina, F.; Luis, S. V.; Ferrer, P.; Costero, A. M.; Marco, J. A. J. Chem. Res. 1986, 2843-2853.
7. This reagent had already been used for the synthesis of two iodoalkynes in a one-pot procedure: Bonnet, B.; Le Gallic, Y.; Plé, G.; Duhamel, L. Synlett 1993, 1071-1073.
8. (a) Speziale, A. J.; Marco, G. J.; Ratts, K. W. J. Am. Chem. Soc. 1960, 82, 1260.
9. (b) Speziale, A. J.; Ratts, K. W. J. Am. Chem. Soc. 1962, 84, 854-859.
10. (c) Raulet, C.; Levas, E. Bull. Soc. Chim. Fr. 1971, 2598-2606.
11. (d) McIntosh, M. C.; Weinreb, S. M. J. Org. Chem. 1991, 56, 5010-5012.
12. 2 was formed, while yellow-brown solutions were observed (see Ref. 1) when this reagent was generated from dibromomethyltriphenylphosphonium bromide.
13. Here again (see Ref. 1), it is important to quench the reaction with a saturated NaCl solution.
14. It may be necessary at this stage to check that 3 has been effectively converted to 4. If not, different higher temperatures should be tested.
15. 3, 50 MHz): -6.9, 19.4, 21.2, 24.9, 28.1, 32.6, 36.5, 39.9, 49.0, 74.5, 93.6.