Palladium catalysed [4+2]-cycloaddition reactions of (2-iodoaryl)allenes

Tetrahedron Letters

Volumn 37, Issue 24, 1996, Pages 4251-4254

  Grigg, Ronald ^a   Xu, Long He ^a  

^a UNIVERSITY OF LEEDS   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALLENE DERIVATIVE; PALLADIUM;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; OXIDATION; STEREOCHEMISTRY;

EID: 0029952355     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00809-X     Document Type: Article

References (22)

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9. O'Connor, J.M.; Stallman, B.J.; Clark, W.G.; Shu, A.Y.; Spoda, R.E.; Stevenson, T.M.; Dieck, H.A.; J. Org. Chem., 1983, 48, 807-809; An, Z.-W.; Catellani, M.; Chiusoli, G.P.; J. Organomet. Chem., 1990, 397, C31-C32; Kelinin, V.N.; Shostakovsky, M.V.; Ponomaryov, A.B.; Tetrahedron Lett., 1990, 31, 4073-4076. Larock, R.C.; Zenner, J.M.; J. Org. Chem., 1995, 60, 482-483; Larock, R.C.; Guo, L.; Synlett., 1995, 465-466; Larock, R.C.; Yum, E.K.; Doty, M.J.; Sham, K.K.C.; J. Org. Chem., 1995, 60, 3270-3271; Chen, C.-Y.; Lieberman, D.R.; Larsen, R.D.; Reamer, R.A.; Verhoeven, T.R.; Reider, P.J.; Cottrell, I.F.; Houghton, P.G.; Tetrahedron Lett., 1994, 35, 6981-6984; Larock, R.C.; Doty, M.J.; Cacchi, S.; J. Org. Chem., 1993, 58, 4579-4583; Jeschke, T.; Wensbe, D.; Annaby, U.; Gronowitz, S.; Cohen, L.A.; Tetrahedron Lett., 1993, 34, 2823-2826 and 6471-6474.
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11. O'Connor, J.M.; Stallman, B.J.; Clark, W.G.; Shu, A.Y.; Spoda, R.E.; Stevenson, T.M.; Dieck, H.A.; J. Org. Chem., 1983, 48, 807-809; An, Z.-W.; Catellani, M.; Chiusoli, G.P.; J. Organomet. Chem., 1990, 397, C31-C32; Kelinin, V.N.; Shostakovsky, M.V.; Ponomaryov, A.B.; Tetrahedron Lett., 1990, 31, 4073-4076. Larock, R.C.; Zenner, J.M.; J. Org. Chem., 1995, 60, 482-483; Larock, R.C.; Guo, L.; Synlett., 1995, 465-466; Larock, R.C.; Yum, E.K.; Doty, M.J.; Sham, K.K.C.; J. Org. Chem., 1995, 60, 3270-3271; Chen, C.-Y.; Lieberman, D.R.; Larsen, R.D.; Reamer, R.A.; Verhoeven, T.R.; Reider, P.J.; Cottrell, I.F.; Houghton, P.G.; Tetrahedron Lett., 1994, 35, 6981-6984; Larock, R.C.; Doty, M.J.; Cacchi, S.; J. Org. Chem., 1993, 58, 4579-4583; Jeschke, T.; Wensbe, D.; Annaby, U.; Gronowitz, S.; Cohen, L.A.; Tetrahedron Lett., 1993, 34, 2823-2826 and 6471-6474.
12. O'Connor, J.M.; Stallman, B.J.; Clark, W.G.; Shu, A.Y.; Spoda, R.E.; Stevenson, T.M.; Dieck, H.A.; J. Org. Chem., 1983, 48, 807-809; An, Z.-W.; Catellani, M.; Chiusoli, G.P.; J. Organomet. Chem., 1990, 397, C31-C32; Kelinin, V.N.; Shostakovsky, M.V.; Ponomaryov, A.B.; Tetrahedron Lett., 1990, 31, 4073-4076. Larock, R.C.; Zenner, J.M.; J. Org. Chem., 1995, 60, 482-483; Larock, R.C.; Guo, L.; Synlett., 1995, 465-466; Larock, R.C.; Yum, E.K.; Doty, M.J.; Sham, K.K.C.; J. Org. Chem., 1995, 60, 3270-3271; Chen, C.-Y.; Lieberman, D.R.; Larsen, R.D.; Reamer, R.A.; Verhoeven, T.R.; Reider, P.J.; Cottrell, I.F.; Houghton, P.G.; Tetrahedron Lett., 1994, 35, 6981-6984; Larock, R.C.; Doty, M.J.; Cacchi, S.; J. Org. Chem., 1993, 58, 4579-4583; Jeschke, T.; Wensbe, D.; Annaby, U.; Gronowitz, S.; Cohen, L.A.; Tetrahedron Lett., 1993, 34, 2823-2826 and 6471-6474.
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16. Coulson, D.R.; J. Org. Chem., 1973, 38, 1483-1490; Larock, R.C.; Berrios-Pena, N.G.; Fried, C.A.; J. Org. Chem., 1991, 56, 2615-2617; Ma, S.; Negishi, E.-I.; J. Am. Chem. Soc., 1995, 117, 6345-6357.
17. Coulson, D.R.; J. Org. Chem., 1973, 38, 1483-1490; Larock, R.C.; Berrios-Pena, N.G.; Fried, C.A.; J. Org. Chem., 1991, 56, 2615-2617; Ma, S.; Negishi, E.-I.; J. Am. Chem. Soc., 1995, 117, 6345-6357.
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19. All new compounds gave satisfactory microanalytical and spectroscopic data.
20. For other examples of retro-Diels-Alder reactions arising from the use of norbornadiene in palladium catalysed processes but occurring at much higher temperatures see: Liu, C.-H.; Li, C.-S.; Cheng, C.-H.; Organometallics, 1994, 13, 18-20; An, Z.-W.; Catellani, M.; Chiusoli, G.P.; Gazz. Chim. Ital., 1990, 120, 383-385.
21. For other examples of retro-Diels-Alder reactions arising from the use of norbornadiene in palladium catalysed processes but occurring at much higher temperatures see: Liu, C.-H.; Li, C.-S.; Cheng, C.-H.; Organometallics, 1994, 13, 18-20; An, Z.-W.; Catellani, M.; Chiusoli, G.P.; Gazz. Chim. Ital., 1990, 120, 383-385.
22. Reactions were carried out with stirring in a Schlenk tube since allene diffuses readily through an ordinary balloon.