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Relative Stabilities of Spirocyclopropanated Cyclopropyl Cations Sergei I. Kozhushkov,[a]
 

Summary: FULL PAPER
Relative Stabilities of Spirocyclopropanated Cyclopropyl Cations
Sergei I. Kozhushkov,[a]
Thomas Späth,[a]
Monica Kosa,[b]
Yitzhak Apeloig,*[b]
Dmitrii S. Yufit,[c]
and Armin de Meijere*[a]
Keywords: Ab initio calculations / Carbocations / Cyclopropanes / Solvolysis / Spiro compounds
Dispiro[2.0.2.1]hept-1-yl triflate (3), 7-bromo-7-phenyldispi-
ro[2.0.2.1]heptane (4) and 7-chloro-7-phenylsulfanyldispi-
ro[2.0.2.1]heptane (6) were prepared from bicyclopropylid-
ene (5) in 50, 77 and 90% overall yield, respectively. 7-
Bromo-7-cyclopropyldispiro[2.0.2.1]heptane (8) and 7-
bromo-7-methyldispiro[2.0.2.1]heptane (11) were obtained
by hydrobromination of 7-cyclopropylidene- (7) and 7-
methylenedispiro[2.0.2.1]heptane (10) (78 and 95% yield, re-
spectively). Methanolyses of triangulane derivatives 4, 6, and
8 as well as acetolysis of 6 all proceed with retention of the
dispiro[2.0.2.1]heptane skeleton yielding the corresponding

  

Source: Apeloig, Yitzhak - Department of Chemistry, Technion, Israel Institute of Technology

 

Collections: Chemistry