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SHORT COMMUNICATION
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cumvents the electronic and steric restrictions of CRC on
tertiary compounds. The diastereomeric outcome of solvol-
ysis likely depends on the presence of secondary carbo-
cationic stabilization of the forming β-silyl cation and on
the steric constraints of the substrate. The products of the
solvolytic reaction can be used to prepare other fluorinated
cyclopropyl compounds. Thus, this method appears to be a
promising synthetic tool as a gateway to access an array of
fluoroalkyl- and perfluoroalkyl-substituted cyclopropanes.
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Acknowledgments
This work was supported by the National Science Foundation
(NSF) (CAREER Award CHE-0847262) and by Stonehill College.
The authors thank Dr. You-Jun Fu for his assistance in obtaining
HRMS of novel compounds, Dr. Vitaliy Gorbatyuk for assistance
with HOESY analysis, and Dr. William Bailey for the use of his
preparative GC (all of the University of Connecticut). The authors
also acknowledge Trevor Hamlin and Kyle Lambert of the Univer-
sity of Connecticut for useful discussions and technical assistance.
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Received: May 4, 2015
Published Online: May 27, 2015
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