Is metal necessary in the Hunsdiecker-Borodin reaction?

Tetrahedron Letters

Volumn 39, Issue 7, 1998, Pages 699-702

  Naskar, Dinabandhu ^a   Chowdhury, Shantanu ^a   Roy, Sujit ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; HALIDE; METAL; PIPERINE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; DECARBOXYLATION; METHODOLOGY; SYNTHESIS;

EID: 0032509932     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10639-6     Document Type: Article

References (19)

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10. 10. Typical yield 18% from silver cinnamate/bromine, Johnson, R.J.; Ingham, R.K.; Chem. Rev. 1956, 56, 219; improved yield in oxidative halo decarboxylation using stoichiometric PhIO/NBS/acid/60°C h, Graven, A.; Jorgensen, K.A.; Dahl, S.; Stanczak, A.; J. Org. Chem. 1994, 59, 3543.
11. 10. Typical yield 18% from silver cinnamate/bromine, Johnson, R.J.; Ingham, R.K.; Chem. Rev. 1956, 56, 219; improved yield in oxidative halo decarboxylation using stoichiometric PhIO/NBS/acid/60°C h, Graven, A.; Jorgensen, K.A.; Dahl, S.; Stanczak, A.; J. Org. Chem. 1994, 59, 3543.
12. 11. (a) Chowdhury, S.; Roy, S.; Tetrahedron Lett. 1996, 37, 2623;
13. (b) S. Chowdhury, S.; Roy, S.; J. Org. Chem. 1997,62,199.
14. 1H NMR (200 MHz), EIMS (70 eV), FTIR and by comparison with authentic samples wherever possible.
15. 4. Pure piperine was isolated in 38% yield via preparative TLC (MERCK Kieselgel 60 F254, eluent hexane/ethylacetate: 9/1). This product was spectroscopically identical to reported literature (ref. 14, 15).
16. 14. (a) Tsuboi, S.; Takeda, A.; Tetrahedron Lett. 1979, 1043;
17. (b) Normant, H.; Fugeas, C.; Compt. Rend. 1964, 258, 2846;
18. (c) Rugheimer, L.; Chem. Ber. 1882, 15, 1390.
19. 15. Wenkert, E.; Cochran, D.W.; Hagaman, E.W.; Lewis, R.B.; Schell, F.M.; J. Am. Chem. Soc. 1971, 93, 6271.