Beilstein J. Org. Chem.2010,6, No. 4, doi:10.3762/bjoc.6.4
strong hydrogen bond donor [N+–H···] moiety is envisaged to disrupt or severely hinder the strong halogen bonding interactions manifested in the non-HB pyridiniumsalt 9. Slow diffusion of ethyl acetate into the ethanol solution of 3-iodopyridinium chloride gave an X-ray-quality crystal of 10. The
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Graphical Abstract
Scheme 1:
The chemical structures of the salts 1–13.
Beilstein J. Org. Chem.2008,4, No. 44, doi:10.3762/bjoc.4.44
these new conditions (Method A), as well as results obtained under the previously reported conditions using pre-formed pyridiniumsalt 1 and trifluorotoluene as the solvent (Method B, entries 2, 4, and 6).
Benzylations of monoglyme (3a) and Roche ester (3b) were accomplished with similar efficiency
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Graphical Abstract
Figure 1:
Benzyl bromide, benzyl trichloroacetimidate, and 2-benzyloxy-1-methylpyridinium triflate (1).