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Volumn 64, Issue 23, 1999, Pages 8668-8680

X-ray crystallographic study of substituted perhydropyrimidinones. Extreme changes in ring conformation

Author keywords

[No Author keywords available]

Indexed keywords

HETEROCYCLIC COMPOUND; PYRIMIDINONE DERIVATIVE;

EID: 0037994370     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991297q     Document Type: Article
Times cited : (11)

References (49)
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    • note
    • This program was supplied by D. Cremer in a personal communication.
  • 31
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    • note
    • 9a respectively) are quite similar to those for enantiopure (2S)-1 and (2S,5R)-14, as can be seen in Figure 21 and Table 6 (Supporting Information).
  • 32
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    • This situation brings to mind the cyclohexane/cyclopentane contrastable behavior: In the six-membered ring one deals with a ring of essentially well-defined conformation, namely the chair form. By contrast, in the five-membered ring there are no pronounced energy minima. See: Willy, W. E.; Binsch, G.; Eliel, E. L. J. Am. Chem. Soc. 1970, 92, 5394-5402.
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    • note
    • Breaking conjugation at the N-CO segment requires over 15 kcal/mol, whereas a bulky substituent axially disposed in the pyrimidinone ring requires less than 3-5 kcal/mol.
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    • Cambridge Crystallographic Data Centre, Cambridge Structural Database System (CSD), 12 Union Road, Cambridge CB2 1EZ, England, April 1997
    • Cambridge Crystallographic Data Centre, Cambridge Structural Database System (CSD), 12 Union Road, Cambridge CB2 1EZ, England, April 1997.


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