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Synthesis and Applications of Tricarbonyliron Complexes of Dendralenes
Author(s) -
ToombsRuane Henry,
Osinski Nik,
Fallon Thomas,
Wills Cindy,
Willis Anthony C.,
PaddonRow Michael N.,
Sherburn Michael S.
Publication year - 2011
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201100455
Subject(s) - chemistry , cyclopropanation , dihydroxylation , cycloaddition , olefin fiber , conjugated system , stereochemistry , metathesis , salt metathesis reaction , organic chemistry , catalysis , enantioselective synthesis , polymer , polymerization
[3]Dendralene and [4]dendralene are converted smoothly into tricarbonyliron complexes. The structures of four complexes analyzed by DFT and single‐crystal X‐ray analysis show that, in contrast to free hydrocarbons, complexed dendralenes prefer a roughly in‐plane conformation. The complexes are stable towards Fe(CO) 3 group migration up to 150 °C. The synthetic value of Fe(CO) 3 complexation in the dendralene series is demonstrated through a variety of selective synthetic manipulations (Diels–Alder reaction, dipolar cycloaddition , Simmons–Smith cyclopropanation , dihydroxylation, olefin cross metathesis ) that are not achievable by direct transformation of the free hydrocarbons. Application to the synthesis of a previously unreported, highly reactive linear/cross‐conjugated hydrocarbon is also described.