An
efficient approach to synthesis of previously unavailable 2-substituted
difluorocyclobutane building blocks was developed and applied on a
multigram scale. The key step of the synthetic sequence included deoxofluorination
of O-protected 2-(hydroxylmethyl)cyclobutanone. Dissociation
constants (pK
a) and log P values for 2,2-difluorocyclobutaneamine and 2,2-difluorocyclobutanecarboxylic
acid or their derivatives were measured and compared with the values
obtained for the corresponding 3,3-difluorocyclobutane derivatives
and nonfluorinated counterparts. Three-dimensional structures of 2,2-
and 3,3-difluorocyclobutanamines were compared using exit vector plot
analysis of X-ray crystallographic data.
Läßt man auf das Bis‐(dialkoxy‐thiophosphoryD‐trisulfid (I) Diazomethan (II) in sechsfachem Überschuß einwirken, dann wird eine Methylengruppe zwischen die Trisulfidkette eingeschoben.
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