The 'Hirao reduction' revisited: A procedure for the synthesis of terminal vinyl bromides by the reduction of 1,1-dibromoalkenes

Tetrahedron Letters

Volumn 41, Issue 17, 2000, Pages 3215-3219

  Abbas, Sahar ^a   Hayes, Christopher J ^a   Worden, Stephen ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALKENE DERIVATIVE; BROMINE DERIVATIVE; PHOSPHATE; TRIETHYLAMINE; TRIPHENYLPHOSPHINE; VINYL DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; METHODOLOGY; REACTION ANALYSIS; REDUCTION; SYNTHESIS;

EID: 0034701604     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00353-1     Document Type: Article

References (14)

1. Matsumoto, M.; Kuroda, K. Tetrahedron Lett. 1980, 21, 4021 and references cited therein.
2. Uenishi, J.; Kawahama, R.; Shiga, Y.; Yonemitsu, O. Tetrahedron Lett. 1996, 37, 6759.
3. Takai, K.; Nitta, K.; Utimoto, K. J. Am. Chem. Soc. 1986, 108, 7408.
4. (a) Hirao, T.; Masunaga, T.; Ohshiro, Y.; Agawa, T. J. Org. Chem. 1981, 46, 3745;
5. (b) Hirao, T.; Masunaga, T.; Yamada, N.; Ohshiro, Y.; Agawa, T. Bull. Chem. Soc. Jpn. 1982, 55, 909.
6. Rossi, R.; Carpita, A.; Lippolis, V. Synth. Commun. 1991, 21, 333.
7. Abbas, S.; Hayes, C. J. Synlett 1999, 1124.
8. Ramirez, F.; Desai, N. B.; McKelvie, N. J. Am. Chem. Soc. 1962, 84, 1745.
9. Meijs, G.; Doyle, I. R. J. Org. Chem. 1985, 50, 3713.
10. Zefirov, N. S.; Makhon'kov, D. I. Chem. Rev. 1982, 82, 615.
11. Corey, E. J.; Fuchs, P. L. Tetrahedron Lett. 1972, 3769.
12. These possibilities were also proposed, and subsequently disproved in the analogous reduction of gem-dibromocyclopropanes (see Ref. 8).
13. For the use of compounds containing P-H bonds in radical processes, see: Graham, S. R.; Murphy, J. A.; Coates, D. Tetrahedron Lett. 1999, 40, 2415 and references cited therin.
14. When the vinyl bromide products were re-subjected to the reaction conditions, no formation of the corresponding acetylene was observed. We therefore conclude that the acetylene products are formed from an intermediate formed during the course of the reaction.