In:
Collection of Czechoslovak Chemical Communications, Institute of Organic Chemistry & Biochemistry, Vol. 67, No. 9 ( 2002), p. 1345-1358
Abstract:
Nucleophilic opening of the epoxide ring in 6-oxabicyclo[3.1.0]hexane ( 1 ) with ethenylmagnesium bromide was employed for the preparation of 2-ethenylcyclopentan-1-ol ( 2 ). Radical addition of perfluoroalkyl iodides 3 to alcohol 2 afforded (polyfluoroiodoalkyl)cyclopentanols 4 , which were deiodinated with tributylstannane to (polyfluoroalkyl)cyclopentanols 5 , followed by dehydration with Nafion-H to the target (polyfluoroalkyl)cyclopentenes 6 , which are potential intermediates for fluorous chemistry. Attempts to synthesize (polyfluoroalkyl)cyclopentadienes or bis(polyfluoroalkyl)cyclopentadienes failed due to the exclusive formation of unexpected side product, polyfluoroiodoalkanol 7 , in the course of radical addition of perfluoroalkyl iodides 3 to ethenylcyclopentenol ( 8 ) or diethenylcyclopentanediol ( 9 ), respectively.
Type of Medium:
Online Resource
ISSN:
0010-0765
,
1212-6950
DOI:
10.1135/cccc20021345
Language:
English
Publisher:
Institute of Organic Chemistry & Biochemistry
Publication Date:
2002
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