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Synthesis and Reactions of Trifluorovinylferrocene
Author(s) -
Roemer Max,
Lentz Dieter
Publication year - 2008
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.200800834
Subject(s) - chemistry , cyclobutane , stille reaction , nucleophile , cycloaddition , derivative (finance) , hydrolysis , yield (engineering) , medicinal chemistry , benzophenone , crystal structure , stereochemistry , organic chemistry , polymer , catalysis , materials science , financial economics , economics , metallurgy , ring (chemistry)
Trifluorovinylferrocene ( 1 ) is obtained in high yield by a Stille coupling of iodoferrocene with tributyltrifluorovinylstannane. [2+2] Cycloaddition of 1 yields the cyclobutane derivatives 2a and 2b under mild conditions. At higher temperature a defluoration reaction takes place yielding the cyclobutane derivative 3 under inert conditions whereas in the presence of air and water the cyclobuta‐1,2‐dion derivative 4 is formed presumably by an unusual hydrolysis of an aliphatic difluoromethylene group. Nucleophilic attack of the CF 2 group of 1 yields specifically the trans isomer of 1,2‐Diferrocenyl‐1,2‐difluoroethene 5 . The crystal and molecular structures of 1 , 2a , 2b , 3 and 5 were elucidated by X‐ray diffraction. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)