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1
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1. Sterner, O.; Steffan, B.; Steglich, W. Tetrahedron 1987, 43, 1075-1082.
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Sterner, O.1
Steffan, B.2
Steglich, W.3
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3. Steglich, W.; Bauer, H.; Große-Bley, M.; Jeschke, R.; Josten, J.; Klein, J. J. Heterocycl. Chem. 1990, 27, 107-110.
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Bauer, H.2
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Jeschke, R.4
Josten, J.5
Klein, J.6
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5
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0012010455
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1) the synthesis of only one monocyclic unsaturated 2H-azepine had been reported: Narasimhan, K.; Kumar, P. R. Heterocycles 1984, 22, 2751-2755.
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Heterocycles
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Narasimhan, K.1
Kumar, P.R.2
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6
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8744283180
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1H NMR spectrum, IR and MS data and an elemental analysis. Our attempts to reproduce the proclaimed synthesis failed. Also, the reported boiling points of the highly phenyl-substituted synthetic intermediates appear to be unrealistically low. Meanwhile, the syntheses of some other substituted 2H-azepines have been reported: a) Albini, A.; Bettinetti, G.; Minoli, G. J. Am. Chem. Soc. 1991, 113, 6928-6934;
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Albini, A.1
Bettinetti, G.2
Minoli, G.3
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7
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0025740172
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b) Satake, K.; Okuda, R.; Hashimoto, M.; Fujiwara, Y.; Watadani, I.; Okamoto, H.; Kimura, M.; Morosawa, S. J. Chem. Soc. Chem. Commun. 1991, 1154-1156;
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Satake, K.1
Okuda, R.2
Hashimoto, M.3
Fujiwara, Y.4
Watadani, I.5
Okamoto, H.6
Kimura, M.7
Morosawa, S.8
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8
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37049083977
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c) Satake, K.; Okuda, R.; Hashimoto, M.; Fujiwara, Y.; Okamoto, H.; Kimura, M.; Morosawa, S. J. Chem. Soc. Perkin Trans. 1 1994, 1753-1757.
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J. Chem. Soc. Perkin Trans. 1
, pp. 1753-1757
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Satake, K.1
Okuda, R.2
Hashimoto, M.3
Fujiwara, Y.4
Okamoto, H.5
Kimura, M.6
Morosawa, S.7
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9
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0011974673
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6. Hamprecht, D.; Polborn, K.; Steglich, W. Angew. Chem. 1995, 707, 1639-1641; Angew. Chem. Int. Ed. Engl. 1995, 34, 1469-1471.
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Angew. Chem.
, vol.707
, pp. 1639-1641
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Hamprecht, D.1
Polborn, K.2
Steglich, W.3
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10
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33748968516
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6. Hamprecht, D.; Polborn, K.; Steglich, W. Angew. Chem. 1995, 707, 1639-1641; Angew. Chem. Int. Ed. Engl. 1995, 34, 1469-1471.
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Angew. Chem. Int. Ed. Engl.
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13
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0012014765
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9. Hollitzer O.; Seewald, A.; Steglich, W. Angew. Chem. 1976, 88, 480-481; Angew. Chem. Int. Ed. Engl. 1976, 75, 480-481; Wild, H.; Mohrs, K.; Niewöhner, U.; Steglich, W. Liebigs Ann. Chem. 1986, 1548-1567.
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Angew. Chem.
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Hollitzer, O.1
Seewald, A.2
Steglich, W.3
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14
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0009673851
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9. Hollitzer O.; Seewald, A.; Steglich, W. Angew. Chem. 1976, 88, 480-481; Angew. Chem. Int. Ed. Engl. 1976, 75, 480-481; Wild, H.; Mohrs, K.; Niewöhner, U.; Steglich, W. Liebigs Ann. Chem. 1986, 1548-1567.
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15
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84985231302
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9. Hollitzer O.; Seewald, A.; Steglich, W. Angew. Chem. 1976, 88, 480-481; Angew. Chem. Int. Ed. Engl. 1976, 75, 480-481; Wild, H.; Mohrs, K.; Niewöhner, U.; Steglich, W. Liebigs Ann. Chem. 1986, 1548-1567.
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Liebigs Ann. Chem.
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Wild, H.1
Mohrs, K.2
Niewöhner, U.3
Steglich, W.4
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16
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85082723443
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10. Prepared from aldehydes and propargyl aluminium reagents according to Bestmann, H. J.; Schobert, R. Synthesis 1989, 419-423; see also Läuger, P.; Prost, M.; Charlier, R. Helv. Chim. Acta 1959, 42, 2379-2393; Bac, N. V.; Langlois, Y. Tetrahedron Lett. 1988, 29, 2819-2822.
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Synthesis
, pp. 419-423
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Bestmann, H.J.1
Schobert, R.2
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17
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84984085095
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10. Prepared from aldehydes and propargyl aluminium reagents according to Bestmann, H. J.; Schobert, R. Synthesis 1989, 419-423; see also Läuger, P.; Prost, M.; Charlier, R. Helv. Chim. Acta 1959, 42, 2379-2393; Bac, N. V.; Langlois, Y. Tetrahedron Lett. 1988, 29, 2819-2822.
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Helv. Chim. Acta
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, pp. 2379-2393
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Läuger, P.1
Prost, M.2
Charlier, R.3
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18
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0011973580
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10. Prepared from aldehydes and propargyl aluminium reagents according to Bestmann, H. J.; Schobert, R. Synthesis 1989, 419-423; see also Läuger, P.; Prost, M.; Charlier, R. Helv. Chim. Acta 1959, 42, 2379-2393; Bac, N. V.; Langlois, Y. Tetrahedron Lett. 1988, 29, 2819-2822.
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Tetrahedron Lett.
, vol.29
, pp. 2819-2822
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Bac, N.V.1
Langlois, Y.2
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19
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37049081914
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11. Kanakam, C. C.; Mani, N. S.; Ramanathan, H.; Subba Rao, G. S. R. J. Chem. Soc., Perkin Trans. 1 1989, 1907-1913.
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Kanakam, C.C.1
Mani, N.S.2
Ramanathan, H.3
Subba Rao, G.S.R.4
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20
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0037768402
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12. Reviews: Jurczak, J.; Golebiowski, A. Chem. Rev. 1989, 89, 149-164; Reetz, M. T. Angew. Chem. 1991, 103, 1559-1573, Angew. Chem. Int. Ed. Engl. 1531-1546.
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Jurczak, J.1
Golebiowski, A.2
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21
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0037768402
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12. Reviews: Jurczak, J.; Golebiowski, A. Chem. Rev. 1989, 89, 149-164; Reetz, M. T. Angew. Chem. 1991, 103, 1559-1573, Angew. Chem. Int. Ed. Engl. 1531-1546.
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Angew. Chem.
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Reetz, M.T.1
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22
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0037768402
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12. Reviews: Jurczak, J.; Golebiowski, A. Chem. Rev. 1989, 89, 149-164; Reetz, M. T. Angew. Chem. 1991, 103, 1559-1573, Angew. Chem. Int. Ed. Engl. 1531-1546.
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Angew. Chem. Int. Ed. Engl.
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23
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49549138922
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13. Corey, E. J.; Suggs, J. W. Tetrahedron Lett. 1975, 2647-2650; Piancatelli, G.; Scettri, A.; D'Auria, M. Synthesis 1982, 245-258.
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(1975)
Tetrahedron Lett.
, pp. 2647-2650
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Corey, E.J.1
Suggs, J.W.2
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24
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85037711539
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13. Corey, E. J.; Suggs, J. W. Tetrahedron Lett. 1975, 2647-2650; Piancatelli, G.; Scettri, A.; D'Auria, M. Synthesis 1982, 245-258.
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(1982)
Synthesis
, pp. 245-258
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Piancatelli, G.1
Scettri, A.2
D'Auria, M.3
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25
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0011976313
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2O (Moroder, L; Hallett, A.; Wünsch, E.; Keller, O.; Wersin, G. Hoppe-Seyler's Z. Physiol. Chem. 1976, 357, 1651-1653).
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(1963)
Physiol. Chem.
, vol.333
, pp. 108-113
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Wünsch, E.1
Zwick, A.2
Hoppe-Seyler's, Z.3
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26
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0017192271
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2O (Moroder, L; Hallett, A.; Wünsch, E.; Keller, O.; Wersin, G. Hoppe-Seyler's Z. Physiol. Chem. 1976, 357, 1651-1653).
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(1976)
Physiol. Chem.
, vol.357
, pp. 1651-1653
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Moroder, L.1
Hallett, A.2
Wünsch, E.3
Keller, O.4
Wersin, G.5
Hoppe-Seyler's, Z.6
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28
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12644312578
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16. Mancuso, A. J.; Huang, S.-L.; Swern, D. J. Org. Chem. 1978, 43, 2480-2482.
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J. Org. Chem.
, vol.43
, pp. 2480-2482
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Mancuso, A.J.1
Huang, S.-L.2
Swern, D.3
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30
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85030210125
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note
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7b
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31
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0001254713
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19. This is in accord with calculations on the nature of [1,5]-sigmatropic migrations in cycloheptatriene which indicate a charge separation in the transition state: Kahn, S. D.; Hehre, W. J.; Rondan, N. G.; Houk, K. N. J. Am. Chem. Soc. 1985, 107, 8291-8292
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J. Am. Chem. Soc.
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Kahn, S.D.1
Hehre, W.J.2
Rondan, N.G.3
Houk, K.N.4
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32
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0001582498
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20. 6e was obtained by Swern oxidation of N-Boc-2-amino-2-methylpropanol according to the procedure of Luly, J. R.; Dellaria, J. F.; Plattner, J. J.; Soderquist, J. L.; Yi, N. J. Org. Chem. 1987, 52, 1487-1492.
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J. Org. Chem.
, vol.52
, pp. 1487-1492
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Luly, J.R.1
Dellaria, J.F.2
Plattner, J.J.3
Soderquist, J.L.4
Yi, N.5
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33
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85030210437
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note
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22 and conversion to the THP ether 21 by reaction with dihydropyran and cat. PPTS.
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35
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84982062445
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23. ter Borg, A. P.; Kloosterziel, H.; van Meurs, N. Rec. Trav. Chim. 1963, 82, 717-740.
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Rec. Trav. Chim.
, vol.82
, pp. 717-740
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Ter Borg, A.P.1
Kloosterziel, H.2
Van Meurs, N.3
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36
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33744586503
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24. Miyashita, N.; Yashikoshi, A.; Grieco, P. A. J. Org. Chem. 1977, 42, 3772-3774.
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J. Org. Chem.
, vol.42
, pp. 3772-3774
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Miyashita, N.1
Yashikoshi, A.2
Grieco, P.A.3
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37
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0000340426
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25 Lindlar, H; Dubuis, R. Org. Synth., Coll. Vol. 5, 1975, 880-886
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(1975)
Org. Synth., Coll. Vol. 5
, vol.5
, pp. 880-886
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Lindlar, H.1
Dubuis, R.2
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