Synthesis of epithio compounds and thiols in the β-pinene and δ3-carene series

Sulfur Letters

Volumn 24, Issue 5, 2001, Pages 213-222

  Candela, Karine ^a   Fellous, Roland ^a   Joulain, Daniel ^a  

^a UNIVERSITÉ CÔTE D'AZUR   (France)

Author keywords

Epithio compounds; Sulfur containing monoterpenes; Thioepoxidation; Thiols

Indexed keywords

10 MERCAPTOPINENE; 2, 10 EPITHIOPINANE; 2,10 EPOXYPINANE; 3 MERCAPTOCARANE; 3,4 EPITHIOCARANE; 3,4 EPOXYCARANE; ALKANE DERIVATIVE; BETA PINENE; ETHYLENE OXIDE DERIVATIVE; FORMAMIDE DERIVATIVE; TERPENE DERIVATIVE; THIOL DERIVATIVE; TRIFLUOROACETIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL ANALYSIS; CHEMICAL COMPOSITION; EPOXIDATION; GAS CHROMATOGRAPHY; MASS SPECTROMETRY; POLARIMETRY; REDUCTION; SYNTHESIS;

EID: 0035760656     PISSN: 02786117     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (25)

1. Boelens, M.H. (1993) Perf. Flavorist, 18, 29.
2. Lawrence, B.M. (1998) Perf. Flavorist, 23, 47.
3. Tangestaninejad, S. and Mirkhani, V. (1999) J. Chem. Res., Synop., 370.
4. Takido, T. and Kobayashi, Y. (1986) Synthesis, 779.
5. Chan, T.H. and Finkenbine, J.R. (1972) J. Amer. Chem. Soc., 94(8), 2880.
6. Fedyunina, I.V. Nikitina, L.E. and Plemenkov, V.V. (1992) Chem. Nat. Compd. (Engl. Transl.), 28, 433; (1992) Khim. Prir. Soedin., 5, 497.
7. Fedyunina, I.V. Nikitina, L.E. and Plemenkov, V.V. (1992) Chem. Nat. Compd. (Engl. Transl.), 28, 433; (1992) Khim. Prir. Soedin., 5, 497.
8. Fedyunina, I.V. and Nikitina, L.E. (1993) Chem. Nat. Compd. (Engl. Transl.), 29, 600: (1993) Khim. Prir. Soedin., 5, 677.
9. Fedyunina, I.V. and Nikitina, L.E. (1993) Chem. Nat. Compd. (Engl. Transl.), 29, 600: (1993) Khim. Prir. Soedin., 5, 677.
10. Nuretdinova, O.N. Bakaleinik, G.A. and Arbuzov, B.A. (1975) Izv. Akad. Nauk SSSR, Ser. Khim., 4, 962; (1975) Chem. Abstr., 83, 97586.
11. Nuretdinova, O.N. Bakaleinik, G.A. and Arbuzov, B.A. (1975) Izv. Akad. Nauk SSSR, Ser. Khim., 4, 962; (1975) Chem. Abstr., 83, 97586.
12. Demole, E. and Enggist, P. (1982) Helv. Chim. Acta, 65, 1785.
13. Sanders, M. (1966) Chem. Rev., 297.
14. Iranpoor, N. and Kazemi, F. (1996) Synthesis, 821.
15. Iranpoor, N. and Kazemi, F. (1997) Tetrahedron, 53, 11377.
16. Mohammadpoor-Baltork, I. and Aliyan, H. (1998) Synth. Commun., 28, 3943.
17. Crombie, L. Crombie, W. M. L. Jamieson, S. V. and Palmer, C. J. Acid-catalysed Terpenylations of olivetol in the Synthesis of Cannabinoids, (1988) J.C.S. Perkin Trans. 1., 1243.
18. Cocker, W. and Grayson, D. H. The Chemistry of Terpenes. Part XIX. Reactions of (+)-3α,4α-Epoxycrane with Halogen Acids and Acetic Acid, (1975) J.C.S. Perkin Trans. 1., 1217.
19. Rauchschwalbe, G. and Schlosser, M. (1975) Helv. Chim. Acta, 58, 1094.
20. Samitov, Y.Y. and Nuretdinova, O.N. (1976) Izv. Akad. Nauk SSSR, Ser. Khim., 12, 2696; (1976) Chem. Abstr., 86, 171609.
21. Samitov, Y.Y. and Nuretdinova, O.N. (1976) Izv. Akad. Nauk SSSR, Ser. Khim., 12, 2696; (1976) Chem. Abstr., 86, 171609.
22. Gadras, A. Dunogues, J. and Calas, R. (1984) J. Org. Chem., 49, 442.
23. Tsay, S.C. Lin, L.C and Furth, P.A. (1993) Synthesis, 329.
24. Janes, J.F. Marr, I.M. and Unwin, N. (1993) Flavour Fragrance J., 8, 289.
25. Trans-2,10-epoxy-pinane 1 and trans-3,4-epoxy-carane 2 were obtained by "Payne oxidation": Payne, G.B. Deming, P.H. and Williams, P.H. (1961) J. Org. Chem., 26, 659.