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Volumn 52, Issue 33, 1996, Pages 10883-10902

Optically active 2H-azepines: Synthesis and rearrangement into their 3H-isomers

Author keywords

[No Author keywords available]

Indexed keywords

AZEPINE DERIVATIVE;

EID: 0030581367     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00629-1     Document Type: Article
Times cited : (25)

References (38)
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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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    • 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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    • 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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    • note
    • 7b
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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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    • note
    • 22 and conversion to the THP ether 21 by reaction with dihydropyran and cat. PPTS.


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