Synthesis of macrocyclic ketones by repeatable two-carbon ring expansion reactions

Chimia

Volumn 57, Issue 4, 2003, Pages 196-199

  Nagel, Matthias ^a   Fráter, Georg ^b   Hansen, Hans Jürgen ^c  

^a SWISS FEDERAL LABORATORIES FOR MATERIALS SCIENCE AND TECHNOLOGY   (Switzerland)

^b GIVAUDAN SCHWEIZ AG   (Switzerland)

^c UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

Dynamic gas phase thermo isomerization; Hydroxyallyl radicals; Macrocyclic ketones; Ring expansions

Indexed keywords

ALKANONE; FUNCTIONAL GROUP; KETONE DERIVATIVE; MACROCYCLIC COMPOUND; MUSCONE; MUSK; VINYL DERIVATIVE;

CONFERENCE PAPER; GAS; HIGH TEMPERATURE; ISOMERISM; REACTION ANALYSIS; REACTOR; REPRODUCIBILITY; SYNTHESIS; THERMAL EXPOSURE;

EID: 0038751940     PISSN: 00094293     EISSN: None     Source Type: Journal    
DOI: 10.2533/000942903777679398     Document Type: Conference Paper

References (16)

1. a) M. Karpf, Angew. Chem. Int. Ed. Engl. 1986, 25, 414, and references therein;
2. b) R.F.C. Brown, 'Pyrolytic Methods in Organic Chemistry', Academic Press, New York, 1981, and references therein.
3. For more general reviews on thermal short contact time reactions and synthetic applications of gas phase flash vacuum pyrolysis techniques, see also a) Y. Vallée (Ed.), 'Gas Phase Reactions in Organic Synthesis', Gordon & Breach Science Publishers, Amsterdam, 1997; b) H. McNab, Contemp. Org. Synth. 1996, 3, 373, and references therein; c) J.I.G. Cadogen, C.L. Hickson, H. McNab, Tetrahedron 1986, 42, 2135; d) U.E. Wiersum, Aldrichimica Acta 1984, 17, 31.
4. For more general reviews on thermal short contact time reactions and synthetic applications of gas phase flash vacuum pyrolysis techniques, see also a) Y. Vallée (Ed.), 'Gas Phase Reactions in Organic Synthesis', Gordon & Breach Science Publishers, Amsterdam, 1997; b) H. McNab, Contemp. Org. Synth. 1996, 3, 373, and references therein; c) J.I.G. Cadogen, C.L. Hickson, H. McNab, Tetrahedron 1986, 42, 2135; d) U.E. Wiersum, Aldrichimica Acta 1984, 17, 31.
5. For more general reviews on thermal short contact time reactions and synthetic applications of gas phase flash vacuum pyrolysis techniques, see also a) Y. Vallée (Ed.), 'Gas Phase Reactions in Organic Synthesis', Gordon & Breach Science Publishers, Amsterdam, 1997; b) H. McNab, Contemp. Org. Synth. 1996, 3, 373, and references therein; c) J.I.G. Cadogen, C.L. Hickson, H. McNab, Tetrahedron 1986, 42, 2135; d) U.E. Wiersum, Aldrichimica Acta 1984, 17, 31.
6. For more general reviews on thermal short contact time reactions and synthetic applications of gas phase flash vacuum pyrolysis techniques, see also a) Y. Vallée (Ed.), 'Gas Phase Reactions in Organic Synthesis', Gordon & Breach Science Publishers, Amsterdam, 1997; b) H. McNab, Contemp. Org. Synth. 1996, 3, 373, and references therein; c) J.I.G. Cadogen, C.L. Hickson, H. McNab, Tetrahedron 1986, 42, 2135; d) U.E. Wiersum, Aldrichimica Acta 1984, 17, 31.
7. a) M. Nagel, H.-J. Hansen, Helv. Chim. Acta 2000, 83, 1022;
8. b) M. Nagel, H.-J. Hansen, Synlett 2002, 692.
9. a) M. Nagel, H.-J. Hansen, G. Fráter, Synlett 2002, 275, and references therein;
10. b) M. Nagel, H.-J. Hansen, G. Fráter, Synlett 2002, 280, and references therein;
11. c) G. Fráter, M. Nagel, (Givaudan SA), EP 1236707-A1, 2002, Prior. 22. Feb. 2001 [Chem. Abstr. 2002, 137, 201099; AN 2002:671899];
12. c) G. Fráter, M. Nagel, (Givaudan SA), EP 1236707-A1, 2002, Prior. 22. Feb. 2001 [Chem. Abstr. 2002, 137, 201099; AN 2002:671899];
13. d) M. Nagel, Ph. D. Thesis, Universität Zürich, 2001;
14. e) Presented in part at the Fall Meeting 2002 of the Swiss Chemical Society in Basel (cf. Abstract 96, Chimia 2002, 56, 352).
15. V. Dimitrov, S. Bratovanov, S. Simova, K. Kostova, Tetrahedron Letters 1994, 35, 6713; for a more detailed description, see also [4].
16. R.W. Thies, J. E. Billigmeier, J. Am Chem. Soc. 1974, 96, 200.