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Volumn 72, Issue 25, 2007, Pages 9439-9447

Reactions of cyclopropanone acetals with alkyl azides: Carbonyl addition versus ring-opening pathways

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CHEMICAL BONDS; KETONES; MOLECULAR STRUCTURE; POSITIVE IONS;

EID: 36849090588     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0711034     Document Type: Article
Times cited : (18)

References (89)
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    • For an outstanding recent review of alkyl azide chemistry, see
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    • (2005) Angew. Chem., Int. Ed , vol.44 , pp. 5188-5240
    • Bräse, S.1    Gil, C.2    Knepper, K.3    Zimmermann, V.4
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    • Attack of nucleophiles at the terminal end of an azide, i.e., as seen in the Staudinger reaction, is known: Nyffeler, P. T.; Liang, C. H.; Koeller, K. M.; Wong, C. H. J. Am. Chem. Soc. 2002, 124, 10773-10778 and references cited therein.
    • Attack of nucleophiles at the terminal end of an azide, i.e., as seen in the Staudinger reaction, is known: Nyffeler, P. T.; Liang, C. H.; Koeller, K. M.; Wong, C. H. J. Am. Chem. Soc. 2002, 124, 10773-10778 and references cited therein.
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    • Inclusion of solvent (dichloromethane) via the IEFPCM algorithm in Gaussian03 gave a similar trend with the differences in coefficients being 0.12 for methyl azide, 0.21 for a, 0.08 for b, and 0.07 for c.
    • Inclusion of solvent (dichloromethane) via the IEFPCM algorithm in Gaussian03 gave a similar trend with the differences in coefficients being 0.12 for methyl azide, 0.21 for a, 0.08 for b, and 0.07 for c.


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