A Novel and Highly Efficient Two-Carbon Ring Expansion

Organic Letters

Volumn 5, Issue 22, 2003, Pages 4211-4213

  Rüedi, Georg ^a   Nagel, Matthias ^a,b   Hansen, Hans Jürgen ^a  

^a UNIVERSITY OF ZURICH   (Switzerland)

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

Author keywords

[No Author keywords available]

Indexed keywords

ALKANONE; CARBON;

ARTICLE; ATOMIC PARTICLE; CHEMICAL REACTION; DYNAMIC GAS PHASE THERMOISOMERIZATION; GAS; ISOMERISM;

EID: 17144472461     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035700y     Document Type: Article

References (29)

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15. Both isomers could be separated by column chromatography and/or by crystallization from 60:1 hexane/AcOEt.
16. 2 (1.4 L/h). At the outlet part of the reactor, the ring expansion product was collected in a cooling trap (-196°C). Purification by flash chromatography (silica gel, 40:1 hexanes/ethyl acetate) gave (E)-2d (2.75 g, 57%) as a first fraction, followed by (Z)-2d (1.35 g, 28%). Both isomers could be crystallized from 60:1 hexanes/ethyl acetate, affording colorless needles. All new compounds were fully characterized.
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18. For leading references on musk odorants, see: (a) Fráter, G.; Bajgrowicz, J. A.; Kraft, P. Tetrahedron 1998, 54, 7633. (b) Fráter, G.; Lamparsky, D. In Perfumes: Art, Science and Technology, Müller, P. M., Lamparsky, D., Eds.; Elsevier: London, New York, 1991; Chapter 20, pp 533-555. (c) Ohloff, G. Riechstoffe und Geruchssinn. Die Molekulare Welt der Düfte; Springer: Berlin, 1990; Chapter 9, pp 195-219. (d) Mookherjee, B. D.; Wilson, R. A. In Fragrance Chemistry: The Science of the Sense of Smell; Theimer, E. T., Ed.; Academic Press: New York, 1982; Chapter 12, pp 433-494.
19. For leading references on musk odorants, see: (a) Fráter, G.; Bajgrowicz, J. A.; Kraft, P. Tetrahedron 1998, 54, 7633. (b) Fráter, G.; Lamparsky, D. In Perfumes: Art, Science and Technology, Müller, P. M., Lamparsky, D., Eds.; Elsevier: London, New York, 1991; Chapter 20, pp 533-555. (c) Ohloff, G. Riechstoffe und Geruchssinn. Die Molekulare Welt der Düfte; Springer: Berlin, 1990; Chapter 9, pp 195-219. (d) Mookherjee, B. D.; Wilson, R. A. In Fragrance Chemistry: The Science of the Sense of Smell; Theimer, E. T., Ed.; Academic Press: New York, 1982; Chapter 12, pp 433-494.
20. For leading references on musk odorants, see: (a) Fráter, G.; Bajgrowicz, J. A.; Kraft, P. Tetrahedron 1998, 54, 7633. (b) Fráter, G.; Lamparsky, D. In Perfumes: Art, Science and Technology, Müller, P. M., Lamparsky, D., Eds.; Elsevier: London, New York, 1991; Chapter 20, pp 533-555. (c) Ohloff, G. Riechstoffe und Geruchssinn. Die Molekulare Welt der Düfte; Springer: Berlin, 1990; Chapter 9, pp 195-219. (d) Mookherjee, B. D.; Wilson, R. A. In Fragrance Chemistry: The Science of the Sense of Smell; Theimer, E. T., Ed.; Academic Press: New York, 1982; Chapter 12, pp 433-494.
21. Decrease in yield might be explained by side reactions taking place in the kugelrohr oven (static conditions) during the evaporation process, which requires higher temperatures for the rather high-boiling substrate 1f.
22. Compounds 3a-d were prepared in excellent yields (90-98%) by conjugate 1,4-addition of the corresponding freshly prepared vinyllithium reagents and cuprous iodide in ether at -78°C, see: (a) Leonard, J.; Mohialdin, S.; Reed, D.; Ryan, G.; Swain, P. A. Tetrahedron 1995, 51, 12843. (b) Linstrumelle, G.; Krieger, J. K.; Whitesides, G. M. Org. Synth. 1976, 55, 103.
23. Compounds 3a-d were prepared in excellent yields (90-98%) by conjugate 1,4-addition of the corresponding freshly prepared vinyllithium reagents and cuprous iodide in ether at -78°C, see: (a) Leonard, J.; Mohialdin, S.; Reed, D.; Ryan, G.; Swain, P. A. Tetrahedron 1995, 51, 12843. (b) Linstrumelle, G.; Krieger, J. K.; Whitesides, G. M. Org. Synth. 1976, 55, 103.
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25. At temperatures below 590°C, almost no conversion occurred, whereas higher temperatures gave rise to a broad variety of low-boiling products.
26. In agreement with this finding, first experiments with optically active (Z)-3b gave racemic 4b as well as racemic starting material (details will be provided in an upcoming publication).
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