Vinylcyclopropylacyl Radicals. Intramolecular Ketene Additions leading to Concise Syntheses of Cyclohexenones

Synlett

Volumn 1997, Issue 1, 1997, Pages 69-70

  Herbert, Nicola ^a   Pattenden, Gerald ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003083685     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-708     Document Type: Article

References (16)

1. See: Chen, L.; Gill, G.B.; Pattenden, G.; Simonian, H.; J. Chem. Soc., Perkin Trans, 1996, 1, 31, and extensive bibliography contained therein.
2. Hayes, C.J.; Pattenden, G.; Tetrahedron Lett., 1996, 37, 271. See also Astley, M.P.; Pattenden, G.; Synthesis, 1992, 101.
3. Hayes, C.J.; Pattenden, G.; Tetrahedron Lett., 1996, 37, 271. See also Astley, M.P.; Pattenden, G.; Synthesis, 1992, 101.
4. For references to α-ketene alkyl radicals see: Tidwell, T.T.; Ketenes, John Wiley, New York, 1995. Davies, A.G.; Hawari, J.A.; Muggleton, B.; Tse, M.; J. Chem. Soc., Perkin Trans. II, 1981, 1132. Davies, A. G.; Sutcliffe, R.; J. Chem. Soc., Perkin Trans. II, 1980, 819. Salem, L.; J. Am. Chem Soc., 1974, 96, 3486. Dauben, W.G.; Cogen, J.M.; Ganzer, G.A.; Behar, V.; J. Am. Chem. Soc., 1991, 113, 5817. Wolff, S.; Agosta, W.C.; J. Am. Chem. Soc., 1983, 105, 1292. Adam, W., Berkessel, A.; Peters, E.; Peters, K.; von Schnering, H.G.; J. Org. Chem., 1985, 50, 2811. Matlin, A.R.; Wolff, S.; Agosta, W.C.; Tetrahedron Lett., 1983, 24, 2961.
5. For references to α-ketene alkyl radicals see: Tidwell, T.T.; Ketenes, John Wiley, New York, 1995. Davies, A.G.; Hawari, J.A.; Muggleton, B.; Tse, M.; J. Chem. Soc., Perkin Trans. II, 1981, 1132. Davies, A. G.; Sutcliffe, R.; J. Chem. Soc., Perkin Trans. II, 1980, 819. Salem, L.; J. Am. Chem Soc., 1974, 96, 3486. Dauben, W.G.; Cogen, J.M.; Ganzer, G.A.; Behar, V.; J. Am. Chem. Soc., 1991, 113, 5817. Wolff, S.; Agosta, W.C.; J. Am. Chem. Soc., 1983, 105, 1292. Adam, W., Berkessel, A.; Peters, E.; Peters, K.; von Schnering, H.G.; J. Org. Chem., 1985, 50, 2811. Matlin, A.R.; Wolff, S.; Agosta, W.C.; Tetrahedron Lett., 1983, 24, 2961.
6. For references to α-ketene alkyl radicals see: Tidwell, T.T.; Ketenes, John Wiley, New York, 1995. Davies, A.G.; Hawari, J.A.; Muggleton, B.; Tse, M.; J. Chem. Soc., Perkin Trans. II, 1981, 1132. Davies, A. G.; Sutcliffe, R.; J. Chem. Soc., Perkin Trans. II, 1980, 819. Salem, L.; J. Am. Chem Soc., 1974, 96, 3486. Dauben, W.G.; Cogen, J.M.; Ganzer, G.A.; Behar, V.; J. Am. Chem. Soc., 1991, 113, 5817. Wolff, S.; Agosta, W.C.; J. Am. Chem. Soc., 1983, 105, 1292. Adam, W., Berkessel, A.; Peters, E.; Peters, K.; von Schnering, H.G.; J. Org. Chem., 1985, 50, 2811. Matlin, A.R.; Wolff, S.; Agosta, W.C.; Tetrahedron Lett., 1983, 24, 2961.
7. For references to α-ketene alkyl radicals see: Tidwell, T.T.; Ketenes, John Wiley, New York, 1995. Davies, A.G.; Hawari, J.A.; Muggleton, B.; Tse, M.; J. Chem. Soc., Perkin Trans. II, 1981, 1132. Davies, A. G.; Sutcliffe, R.; J. Chem. Soc., Perkin Trans. II, 1980, 819. Salem, L.; J. Am. Chem Soc., 1974, 96, 3486. Dauben, W.G.; Cogen, J.M.; Ganzer, G.A.; Behar, V.; J. Am. Chem. Soc., 1991, 113, 5817. Wolff, S.; Agosta, W.C.; J. Am. Chem. Soc., 1983, 105, 1292. Adam, W., Berkessel, A.; Peters, E.; Peters, K.; von Schnering, H.G.; J. Org. Chem., 1985, 50, 2811. Matlin, A.R.; Wolff, S.; Agosta, W.C.; Tetrahedron Lett., 1983, 24, 2961.
8. For references to α-ketene alkyl radicals see: Tidwell, T.T.; Ketenes, John Wiley, New York, 1995. Davies, A.G.; Hawari, J.A.; Muggleton, B.; Tse, M.; J. Chem. Soc., Perkin Trans. II, 1981, 1132. Davies, A. G.; Sutcliffe, R.; J. Chem. Soc., Perkin Trans. II, 1980, 819. Salem, L.; J. Am. Chem Soc., 1974, 96, 3486. Dauben, W.G.; Cogen, J.M.; Ganzer, G.A.; Behar, V.; J. Am. Chem. Soc., 1991, 113, 5817. Wolff, S.; Agosta, W.C.; J. Am. Chem. Soc., 1983, 105, 1292. Adam, W., Berkessel, A.; Peters, E.; Peters, K.; von Schnering, H.G.; J. Org. Chem., 1985, 50, 2811. Matlin, A.R.; Wolff, S.; Agosta, W.C.; Tetrahedron Lett., 1983, 24, 2961.
9. For references to α-ketene alkyl radicals see: Tidwell, T.T.; Ketenes, John Wiley, New York, 1995. Davies, A.G.; Hawari, J.A.; Muggleton, B.; Tse, M.; J. Chem. Soc., Perkin Trans. II, 1981, 1132. Davies, A. G.; Sutcliffe, R.; J. Chem. Soc., Perkin Trans. II, 1980, 819. Salem, L.; J. Am. Chem Soc., 1974, 96, 3486. Dauben, W.G.; Cogen, J.M.; Ganzer, G.A.; Behar, V.; J. Am. Chem. Soc., 1991, 113, 5817. Wolff, S.; Agosta, W.C.; J. Am. Chem. Soc., 1983, 105, 1292. Adam, W., Berkessel, A.; Peters, E.; Peters, K.; von Schnering, H.G.; J. Org. Chem., 1985, 50, 2811. Matlin, A.R.; Wolff, S.; Agosta, W.C.; Tetrahedron Lett., 1983, 24, 2961.
10. For references to α-ketene alkyl radicals see: Tidwell, T.T.; Ketenes, John Wiley, New York, 1995. Davies, A.G.; Hawari, J.A.; Muggleton, B.; Tse, M.; J. Chem. Soc., Perkin Trans. II, 1981, 1132. Davies, A. G.; Sutcliffe, R.; J. Chem. Soc., Perkin Trans. II, 1980, 819. Salem, L.; J. Am. Chem Soc., 1974, 96, 3486. Dauben, W.G.; Cogen, J.M.; Ganzer, G.A.; Behar, V.; J. Am. Chem. Soc., 1991, 113, 5817. Wolff, S.; Agosta, W.C.; J. Am. Chem. Soc., 1983, 105, 1292. Adam, W., Berkessel, A.; Peters, E.; Peters, K.; von Schnering, H.G.; J. Org. Chem., 1985, 50, 2811. Matlin, A.R.; Wolff, S.; Agosta, W.C.; Tetrahedron Lett., 1983, 24, 2961.
11. For references to α-ketene alkyl radicals see: Tidwell, T.T.; Ketenes, John Wiley, New York, 1995. Davies, A.G.; Hawari, J.A.; Muggleton, B.; Tse, M.; J. Chem. Soc., Perkin Trans. II, 1981, 1132. Davies, A. G.; Sutcliffe, R.; J. Chem. Soc., Perkin Trans. II, 1980, 819. Salem, L.; J. Am. Chem Soc., 1974, 96, 3486. Dauben, W.G.; Cogen, J.M.; Ganzer, G.A.; Behar, V.; J. Am. Chem. Soc., 1991, 113, 5817. Wolff, S.; Agosta, W.C.; J. Am. Chem. Soc., 1983, 105, 1292. Adam, W., Berkessel, A.; Peters, E.; Peters, K.; von Schnering, H.G.; J. Org. Chem., 1985, 50, 2811. Matlin, A.R.; Wolff, S.; Agosta, W.C.; Tetrahedron Lett., 1983, 24, 2961.
12. For bibliography see ref. 1. See also: Crich, D.; Yao, Q.; J. Org. Chem., 1996, 61, 3566.
13. 2, -30°C, 72%.
14. All new compounds showed satisfactory spectroscopic data together with microanalytical and/or mass spectrometry data. Typical procedure for conversion of the vinyl cyclopropane 7 into the cyclohexenone 8: A solution of the selenyl ester (50mg, 0.17mmol) in dry degassed benzene (54ml) containing AIBN (28mg, 0.17 mmol) was stirred and heated to reflux. A solution of n-Bu,SnH (99mg, 92μl, 0.34mmol) in dry degassed benzene (2ml) was added dropwise (via a syringe pump) over 2hrs to the heated mixture which was then stirred and heated under reflux for a further 2hrs. After cooling to room temperature the solvent was removed in vacuo and the residue was then purified by chromatography on silica gel eluting with petrol/diethyl ether (5:1) to afford the cyclohexenone 8 (14mg, 0.1mmol, 60%).
15. For structural studies with cyclopropylacyl radicals see: Davies, A.G., Sutcliffe, R., J. Chem. Soc. Perkin Trans. II, 1982, 1483. See also: Zelechonok, Y; Silverman, R.B.; J. Org. Chem., 1992, 57, 5785.
16. For structural studies with cyclopropylacyl radicals see: Davies, A.G., Sutcliffe, R., J. Chem. Soc. Perkin Trans. II, 1982, 1483. See also: Zelechonok, Y; Silverman, R.B.; J. Org. Chem., 1992, 57, 5785.